Comprehensive organic synthesis : selectivity, strategy & efficiency in modern organic chemistry / volume 1, Additions to C-X [pi]-bonds, part 1 / ed. Stuart L. Schreiber

987 Pages·1991·20.68 MB·English

by  Barry Martin Trost

COMPREHENSIVE
ORGANIC SYNTHESIS
Selectivity, Strategy & Efficiency
in Modem Organic Chemistry
Edi tor-in-Chief
BARRY M. TROST
Stanford University, CA, USA
Deputy Edit or-in-Ch ief
IANFLEMING
University of Cambridge, UK
Volume 1
ADDITIONS TO C-X T-BONDS, PART 1
Volume Editor
STUART L. SCHREIBER
Harvard University, Cambridge, MA, USA
PERGAMON PRESS
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British Library Cataloguing in Publication Data
Comprehensive organic synthesis
3. Organic compounds. Synthesis
I. Trost, Barry M. (Barry Martin) 1941-
547.2
Comprehensive organic synthesis: selectivity, strategy and
efficiency in modem organic chemistry/editor[s] Barry M,
Trost, Ian Fleming.
p. cm.
Includes indexes.
Contents: Vol. I. - 2. Additions to C-X[pi]-Bonds - v. 3.
Carbon-carbon sigma-Bond formation - v. 4. Additions
to and substitutions at C-C[pi]-Bonds - v. 5. Combining
C-C[pi]-Bonds - v. 6. Heteroatom manipulation - v. 7.
Oxidation - v. 8. Reduction - v. 9. Cumulative indexes.
3. Organic Compounds - Synthesis I. Trost, Barry M. 1941-
11. Fleming, Ian. 1935-
QD262.C535 1991
547.24~20 90-2662 1
ISBN-13: 978-0-08-040592-6 (Vol 1)
ISBN-IO: 0-08-040592-4 (Vol 1)
ISBN- 0-08-035929-9 (set)
For information on all Pergamon publications
visit our website at books.elsevier.com
Printed and bound in The Netherlands
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Contents
Preface vii
Contributors to Volume 1 ix
Abbreviations xi
Contents of All Volumes xv
Nonstabilized Carbanion Equivalents
1.1 Carbanions of Alkali and Alkaline Earth Cations: (i) Synthesis and Structural 1
Characterization
P. G. WILLIARD, Brown University,P rovidence, RI, USA
1.2 Carbanions of Alkali and Alkaline Earth Cations: (ii) Selectivity of Carbonyl Addition 49
Reactions
D. M. "RYN, [email protected] Roche, Nutley, NJ, USA
1.3 Organoaluminum Reagents 77
J. R. HAUSKE,P fizer Central Research, Groton, CT, USA
1.4 Organocopper Reagents 107
B. H. LIPSHUTZ, University of California, Santa Barbara, CA, USA
1.5 Organotitanium and Organozirconium Reagents 139
C. FERRERI,G . PALUMBO & R. CAPUTO,U niversitd di Napoli, Italy
1.6 Organochromium Reagents 173
N. A. SACCOMANO, Pfizer Central Research, Groton, CT, USA
1.7 Organozinc, Organocadmium and Organomercury Reagents 21 1
P. KNOCHEL, University of Michigan, Ann Arbor, MI, USA
1. a Organocerium Reagents 23 1
T. IMAMOTO, Chiba University,J apan
1.9 Samarium and Ytterbium Reagents 25 1
G. A, MOLANDER, University of Colorado, Boulder, CO, USA
1.10 Lewis Acid Carbonyl Complexation 283
S. SHAMBAYATI & S. L. SCHREIBER, Harvard University, Cambridge,M A, USA
1.11 Lewis Acid Promoted Addition Reactions of Organometallic Compounds 325
M. YAMAGUCHI, Tohoku University, Sendai, Japan
1.12 Nucleophilic Addition to Imines and Imine Derivatives 355
R. A. VOLKMANN, Pfzer Central Research, Groton, CT,U SA
1.13 Nucleophilic Addition to Carboxylic Acid Derivatives 397
B. T. O'NEILL, Pfzer Central Research, Groton, CT, USA
Heteroatom-stabilizedC arbanion Equivalents
2.1 Nitrogen Stabilization 459
R. E. GAWLEY & K. REIN, University of Miami, Coral Gables, FL, USA
2.2 Boron Stabilization 487
A. PELTER & K. SMITH,U niversity College Swansea, UK
2.3 Sulfur Stabilization 505
K. OGURA,C hiba University,J apan
2.4 The Benzoin and Related Acyl Anion Equivalent Reactions 54 1
A. HASSNER, Bar-Ilan University,R amat-Gun, Israel & K. M. L. Rai,
University of Mysore, India
V
vi Contents
2.5 Silicon Stabilization 579
J. S. PANEK, Boston University,M A, USA
2.6 Selenium Stabilization 629
A. KRIEF, Facultbs UniversitairesN otre-Dame de la Paix, Namur,B elgium
Transformationo f the Carbonyl Group into Nonhydroxylic Groups
3.1 Alkene Synthesis 729
S. E. KELLY,P fizer Central Research, Groton, CT,U SA
3.2 Epoxidation and Related Processes 819
J. AUBfi, University of Kansas, Lawrence, KS, USA
3.3 Skeletal Reorganizations: Chain Extension and Ring Expansion 843
P. M.W OVKULICH, Hoffmann-La Roche, Nutley, NJ, USA
Author Index 901
Subject Index 949
Preface
The emergence of organic chemistry as a scientific discipline heralded a new era in human develop
ment. Applications of organic chemistry contributed significantly to satisfying the basic needs for food,
clothing and shelter. While expanding our ability to cope with our basic needs remained an important
goal, we could, for the first time, wony about the quality of life. Indeed, there appears to be an excellent
correlation between investment in research and applications of organic chemistry and the standard of liv-
ing. Such advances arise from the creation of compounds and materials. Continuation of these contribu-
tions requires a vigorous effort in research and development, for which information such as that provided
by the Comprehensive series of Pergamon Press is a valuable resource.
Since the publication in 1979 of Comprehensive Organic Chemistry, it has become an important first
source of information. However, considering the pace of advancements and the ever-shrinking timeframe
in which initial discoveries are rapidly assimilated into the basic fabric of the science, it is clear that a
new treatment is needed. It was tempting simply to update a series that had been so successful. However,
this new series took a totally different approach. In deciding to embark upon Comprehensive Organic
Synthesis, the Editors and Publisher recognized that synthesis stands at the heart of organic chemistry.
The construction of molecules and molecular systems transcends many fields of science. Needs in
electronics, agriculture, medicine and textiles, to name but a few, provide a powerful driving force for
more effective ways to make known materials and for routes to new materials. Physical and theoretical
studies, extrapolations from current knowledge, and serendipity all help to identify the direction in which
research should be moving. All of these forces help the synthetic chemist in translating vague notions to
specific structures, in executing complex multistep sequences, and in seeking new knowledge to develop
new reactions and reagents. The increasing degree of sophistication of the types of problems that need to
be addressed require increasingly complex molecular architecture to target better the function of the re-
sulting substances. The ability to make such substances available depends upon the sharpening of our
sculptors’ tools: the reactions and reagents of synthesis.
The Volume Editors have spent great time and effort in considering the format of the work. The inten-
tion is to focus on transformations in the way that synthetic chemists think about their problems. In terms
of organic molecules, the work divides into the formation of carbon-carbon bonds, the introduction of
heteroatoms, and heteroatom interconversions. Thus, Volumes 1-5 focus mainly on carbon-carbon bond
formation, but also include many aspects of the introduction of heteroatoms. Volumes 6-8 focus on
interconversion of heteroatoms, but also deal with exchange of carbon-carbon bonds for carbon-
heteroatom bonds.
The Editors recognize that the assignment of subjects to any particular volume may be arbitrary in
part. For example, reactions of enolates can be considered to be additions to C-C .rr-bonds. However,
the vastness of the field leads it to be subdivided into components based upon the nature of the bond-
forming process. Some subjects will undoubtedly appear in more than one place.
In attacking a synthetic target, the critical question about the suitability of any method involves selec-
.
tivity: chemo-, regio-, diastereo- and enantio-selectivity Both from an educational point-of-view for the
reader who wants to leam about a new field, and an experimental viewpoint for the practitioner who
seeks a reference source for practical information, an organization of the chapters along the theme of
selectivity becomes most informative.
The Editors believe this organization will help emphasize the common threads that underlie many
seemingly disparate areas of organic chemisq. The relationships among various transformations
becomes clearer md the applicability of transformations across a large number of compound classes
becomes apparent. Thus, it is intended that an integration of many specialized areas such as terpenoid,
heterocyclic, carbohydrate, nucleic acid chemistry, etc. within the more general transformation class will
provide an impetus to the consideration of methods to solve problems outside the traditional ones for any
specialist.
In general, presentation of topics concentrates on work of the last decade. Reference to earlier work,
as necessary and relevant, is made by citing key reviews. All topics in organic synthesis cannot be
treated with equal depth within the constraints of any single series. Decisions as to which aspects of a
vii
viii Preface
topic require greater depth are guided by the topics covered in other recent Comprehensive series. This
new treatise focuses on being comprehensive in the context of synthetically useful concepts.
The Editors and Publisher believe that Comprehensive Organic Synthesis will serve all those who
must face the problem of preparing organic compounds. We intend it to be an essential reference work
for the experienced practitioner who seeks information to solve a particular problem. At the same time,
we must also serve the chemist whose major interest lies outside organic synthesis and therefore is only
an occasional practitioner. In addition, the series has an educational role. We hope to instruct experi-
enced investigators who want to leam the essential facts and concepts of an area new to them. We also
hope to teach the novice student by providing an authoritative account of an area and by conveying the
excitement of the field.
The need for this series was evident from the enthusiastic response from the scientific community in
-
the most meaningful way their willingness to devote their time to the task. I am deeply indebted to an
exceptional board of editors, beginning with my deputy editor-in-chief Ian Fleming, and extending to the
-
entire board Clayton H. Heathcock, Ryoji Noyori, Steven V. Ley, Leo A. Paquette, Gerald Pattenden,
Martin F. Semmelhack, Stuart L. Schreiber and Ekkehard Winterfeldt.
The substance of the work was created by over 250 authors from 15 countries, illustrating the truly in-
ternational nature of the effort. I thank each and every one for the magnificent effort put forth. Finally,
such a work is impossible without a publisher. The continuing commitment of Pergamon Press to serve
the scientific community by providing this Comprehensive series is commendable. Specific credit goes
to Colin Drayton for the critical role he played in allowing us to realize this work and also to Helen
McPherson for guiding it through the publishing maze.
A work of this kind, which obviously summarizes accomplishments, may engender in some the feel-
ing that there is little more to achieve. Quite the opposite is the case. In looking back and seeing how far
we have come, it becomes only more obvious how very much more we have yet to achieve. The vastness
of the problems and opportunities ensures that research in organic synthesis will be vibrant for a very
long time to come.
BARRY M.T ROST
Palo Alto, California
Contributors to Volume 1
Professor J. AuM
Department of Medicinal Chemistry, University of Kansas, Lawrence, KS 66045-2506, USA
Dr R. Caput0
Dipartimento di Chimica Organica e Biologica, Universid di Napoli, Via Mezzocannone 16,
1-80134 Napoli, Italy
Dr C. Ferreri
Dipartimento di Chimica Organica e Biologica, Universid di Napoli, Via Mezzocannone 16,
1-80134 Napoli, Italy
Professor R. E. Gawley
Department of Chemistry, University of Miami, PO Box 2491 18, Coral Gables, FL 33124, USA
Professor A. Hassner
Department of Chemistry, Bar-Ilan University, Ramat-Gan 59100, Israel
Dr J. R. Hauske
Pfker Central Research, Eastern Point Road, Groton, CT 06340, USA
Dr D. M. Huryn
Building 76,H offmann-La Roche Inc, 340 Kingsland Street, Nutley, NJ 071 10-11 99, USA
Professor T. Imamoto
Department of Chemistry, Faculty of Science, Chiba University, Yayoi-cho, Chiba 260, Japan
Dr S. E. Kelly
Pfizer Central Research, Eastern Point Road, Groton, CT 06340, USA
Professor P. Knochel
Department of Chemistry, University of Michigan, Ann Arbor, MI 48109-1055, USA
Professor A. Krief
Departement de Chemie, Facultds Universitaires Notre-Dame de la Paix, Rue de Bruxelles 61,
B-5000 Namur, Belgium
Professor B. H. Lipshutz
Department of Chemistry, University of California, Santa Barbara, CA 93 106, USA
Professor G.A . Molander
Department of Chemistry & Biochemistry, University of Colorado, Campus Box 215, Boulder,
CO 80309-021 5, USA
Professor K. Ogura
Department of Synthetic Chemistry, Chiba University, 1-33 Yayoi-cho, Chiba 260, Japan
Dr B. T. O’Neill
Wizer Central Research, Eastern Point Road, Groton, CT 06340, USA
Dr G. Palumbo
Dipartimento di Chimica Organica e Biologica, Universid di Napoli, Via Mezzocannone 16,
1-80134 Napoli, Italy
Professor J. S. Panek
Department of Chemistry, Boston University, 590 Commonwealth Avenue, Boston, MA 02215, USA
Professor A. Pelter
Department of Chemistry, University College Swansea, Singleton Park, Swansea SA2 8PP, UK
Dr K. M. L. Rai
Department of Chemistry, University of Mysore, Manasa Gangotri, Mysore 570006, India
Mrs K. Rein
Department of Chemistry, University of Miami, PO Box 2491 18, Coral Gables, FL 33 124, USA
Dr N. A. Saccomano
Pfizer Central Research, Eastern Point Road, Groton, CT 06340, USA
ix
X Contributors to Volume 1
Professor S. L. Schreiber
Department of Chemistry, b a r dU niversity, 12 Oxford Street, Cambridge, MA 02138, USA
Mr S. Shambayati
Department of Chemistry, Harvard University, 12 Oxford Street, Cambridge, MA 02138, USA
Professor K. Smith
Deparhnent of Chemistry, University College Swansea,S ingleton Park, Swansea SA2 8PP,U K
Dr R. A. Vollunann
Pfizer Central Research, Eastern Point Road, Groton, CT 06340, USA
Professor P. G. Williard
Department of Chemistry, Brown University, Providence, RI 02912, USA
Dr P. M. Wovkulich
Building 76, H0ffmann-h R O CI~~c 3,4 0 Kingsland Stnet, Nutley, NJ 071 10-1 199, USA
Professor M.Y amaguchi
Department of Chemistry, Faculty of Science, Tohuku University, Aoba, Sendai 980, Japan
Abbreviations
The following abbreviations have been used where relevant. All other abbreviations have been defined
the first time they occur in a chapter.
Techniques
CD circular dichroism
CIDNP chemically induced dynamic nuclear polarization
CNDO complete neglect of differential overlap
CT charge transfer
GLC gas-liquid chromatography
HOMO highest occupied molecular orbital
HPLC high-performance liquid chromatography
ICR ion cyclotron resonance
INDO incomplete neglect of differential overlap
IR infrared
LCAO linear combination of atomic orbitals
LUMO lowest unoccupied molecular orbital
MS mass spectrometry
NMR nuclear magnetic resonance
ORD optical rotatory dispersion
PE photoelectron
SCF self-consistentf ield
TLC thin layer chromatography
uv
ultraviolet
Reagents, solvents, etc.
Ac acetyl
acac acetylacetonate
AIBN 2,2' -azobisisobutyronitrile
Ar aryl
ATP adenosine triphosphate
9-BBN 9-borabicyclo[3 .3.1 jnonyl
9-BBN-H 9-borabicyclo[3 .3.1I nonane
BHT 2,6-di-r-butyl-4-methylphen(oblu tylated hydroxytoluene)
biPY 2,2'-bipyridyl
Bn benzyl
t-BOC t-butoxycarbonyl
BSA N,O-bis(trimethylsily1)acetamide
BSTFA N,O-bis(trimethylsi1y 1)trifluoroacetamide
BTAF benzyltrimethylammonium fluoride
Bz benzoyl
CAN ceric ammonium nitrate
COD 1,5-~yclooctadiene
COT c yclooctatetraene
CP c yclopentadieny l
CP* pentamethylcy clopentadienyl
18-crown-6 1,4,7,10,13,16-hexaoxacyclooctadecane
CSA camphorsulfonic acid
CSI chlorosulfonyl isocyanate
DABCO 1,4-diazabicyclo[2.2.2]octane
DBA dibenzyl ideneacetone
DBN 1,5-diazabicyclo[4.3.O]non-5-ene
DBU 1,8-diazabicyclo[5.4.0]undec-7-ene
xi
xii Abbreviations
DCC dicy c lohexy lcarbodiimide
DDQ 2,3-dichlor0-5,6dicyano-1 , 4-benzoquinone
DEAC diethy laluminum chloride
DEAD diethyl azodicarboxylate
DET diethyl tartrate (+ or -)
DHP dihYdroPYran
DIBAL-H diisobutyl aluminum hydride
diglyme diethylene glycol dimethyl ether
dimsyl Na sodium methylsulfmyhnethide
DIOP 2,3-O-isopropylidene-2,3-dihydroxlyp-- bis (dipheny1phosphino)butane
DIFT diisopropyl tartrate (+ or -)
DMA dimethylacetamide
DMAC dimethylaluminum chloride
DMAD dimethyl acetylenedicarboxylate
DMAP 4dimethylaminopyridine
DME dimethoxy ethane
DMF dimethy lformamide
DMI N,” dimethylimidazolone
DMSO dimethyl sulfoxide
DMTSF dimethyl(methy1thio)sulfonium fluomborate
DPPB 1,4-bis(diphenylphosphino)butane
DPPE 1,2-bis(diphenylphosphino)ethane
DPPF 1,l’- bis(diphenylphosphino)ferrocene
DPPP 1,3-bis(d ipheny1phosphino)pmpane
E+ electrophile
EADC ethylaluminum dichloride
EM3 electron-donating group
EDTA ethylenediaminetetraacetica cid
EEDQ N-ethoxycarbonyl-2-ethoxy-1 ,2-dihydroquinoline
EWG electron-withdrawingg roup
HMPA hexamethylphosphorict riamide
HOBT hydroxyb enzotriazole
IpcBH2 isopinocamphey l borane
Ipc2BH diisopinocampheylborane
KAPA potassium 3-aminopropy larnide
K-selectride potassium tri-s-butylborohydride
LAH lithium aluminum hydride
LDA lithium diisopropylamide
LICA lithium isopropylcyclohexy lamide
LITMP lithium tetramethy lpiperidide
L-selectride lithium ai-s-butylborohydride
LTA lead tetraacetate
MCPBA m-chloroperbenzoica cid
MEM methoxy e thoxy m ethy 1
MEM-Cl P-methoxyethoxymethylc hloride
MMA methyl methacrylate
MMC methylmagnesium carbonate
MOM methoxymethyl
Ms methanesulfonyl
MSA methanesulfonic acid
MsCl methanesulfonyl chloride
MVK methyl vinyl ketone
NBS N-bromosuccinimide
NCS N-chlorosuccinimide