Chiral Lewis Acids

225 Pages·2018·20.17 MB·English

by  Koichi Mikami (eds.)

Topics in Organometallic Chemistry 62
Koichi Mikami Editor
Chiral Lewis
Acids
62
Topics in Organometallic Chemistry
Editorial Board
M. Beller, Rostock, Germany
P.H. Dixneuf, Rennes CX, France
J. Dupont, Porto Alegre, Brazil
A. Fu¨rstner, Mu¨lheim, Germany
F. Glorius, Mu¨nster, Germany
L.J. Gooßen, Kaiserslautern, Germany
T. Ikariya, Tokyo, Japan
S.P. Nolan, Ghent, Belgium
J. Okuda, Aachen, Germany
L.A. Oro, Zaragoza, Spain
M. Willis, Oxford, United Kingdom
Q.-L. Zhou, Tianjin, China
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Koichi Mikami
Editor
Chiral Lewis Acids
With contributions by
(cid:1) (cid:1) (cid:1) (cid:1) (cid:1)
M. Brill Y. Deng M. P. Doyle X. Feng M. Hatano
(cid:1) (cid:1) (cid:1) (cid:1)
K. Ishihara S. Kobayashi N. Kumagai X. Liu
(cid:1) (cid:1) (cid:1) (cid:1)
S. P. Nolan J. Paradies Q. Sha M. Shibasaki
(cid:1) (cid:1)
T. Tsubogo Z. Wang Y. Yamashita
Editor
KoichiMikami
DepartmentofChemicalScienceandEngineering
SchoolofMaterialsandChemicalTechnology
TokyoInstituteofTechnology
Tokyo,Japan
ISSN1436-6002 ISSN1616-8534 (electronic)
TopicsinOrganometallicChemistry
ISBN978-3-319-70804-1 ISBN978-3-319-70806-5 (eBook)
https://doi.org/10.1007/978-3-319-70806-5
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Preface
I write this preface after the announcement of the 2017 Nobel Prize in Chemistry
with the belief that within this book titled “Chiral Lewis Acid Catalyses” there
are several candidates who could be considered for the distinguished title of
NobelLaureateinchemistry.
The Nobel Prize in Chemistry in the early twenty-first century was awarded
to Professors Noyori and Sharpless, and Dr. Knowles for their work on
“Asymmetric Catalyses” of functional group interconversion such as oxidation
and hydrogenation. However, one of the most important processes in organic
synthesis,namelythe“AsymmetricCatalysesofCarbon-CarbonBondFormation”,
hasyettoberecognisedbytheawardoftheNobelPrize.
Chiral Lewis acid catalysts work so well in the main body of carbon-carbon
bond forming reactions such as the Mukaiyama aldol reaction, Friedel-Crafts
reaction, Diels-Alder reaction, and Alder-ene reaction. The Lewis acid catalysts
can increase the regioselectivity, stereoselectivity, and particularly enantios-
electivity of these reactions in addition to accelerating the reaction rate. In this
context, the principles and design concepts of Chiral Lewis Acid Catalysts
are extensively covered in the chapter “The Future of Catalysis by Chiral
Lewis Acids”. Particularly, proof of concept in ligand design is exemplified in a
showcase of peptide ligands for heterobimetallic catalyses (chapter “Chiral
Bimetallic Lewis Acids”). Quite recent progress in chiral Brønsted acid catalysts
(chapter “Chiral Carbophilic Gold Lewis Acid Complexes in Enantioselective
Catalysis”) and chiral metallic Lewis acid catalysts (chapters “Brønsted Acid/
Lewis Base Hybrid Complexes”, “Chiral Alkaline Earth Metal Complexes in
Asymmetric Catalysis” and “Chiral Lewis Acid Rare-Earth Metal Complexes in
EnantioselectiveCatalysis”)oftheconjugatedbasesisalsodiscussedinthisbook.
GoldrushincarbophilicgoldLewisacidcatalysts(chapter“BrønstedAcid/Lewis
Base Hybrid Complexes”) is thus highlighted. Practical applications of alkaline
(earth)(chapter“ChiralAlkalineEarthMetalComplexesinAsymmetricCatalysis”)
and lanthanide (chapter “Chiral Lewis Acid Rare-Earth Metal Complexes in
v
vi Preface
Enantioselective Catalysis”) catalysts are fully covered by the specialists. Finally
inthechapter“ChiralBorane-BasedLewisAcidsforMetalFreeHydrogenations”
the future direction of “frustrated” Lewis acid/base pair catalysts is foreseen in
asymmetriccatalyses.
Withthisinminditismybeliefthatcontinuingprogress inthisfieldof“Chiral
Lewis Acid Catalysis” will be rewarded with the Nobel Prize in Chemistry in the
nearfuture.
Tokyo,Japan KoichiMikami
Contents
TheFutureofCatalysisbyChiralLewisAcids. . . . . . . . . . . . . . . . . . 1
QiangSha,YongmingDeng,andMichaelP.Doyle
ChiralBimetallicLewisAcids. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 27
MasakatsuShibasakiandNaoyaKumagai
ChiralCarbophilicGoldLewisAcidComplexesinEnantioselective
Catalysis. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 51
MarcelBrillandStevenP.Nolan
BrønstedAcid/LewisBaseHybridComplexes. . . . . . . . . . . . . . . . . . . 91
ManabuHatanoandKazuakiIshihara
ChiralAlkalineEarthMetalComplexesinAsymmetricCatalysis. . . . 121
YasuhiroYamashita,TetsuTsubogo,andSh(cid:1)uKobayashi
ChiralLewisAcidRare-EarthMetalComplexesinEnantioselective
Catalysis. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 147
XiaomingFeng,ZhenWang,andXiaohuaLiu
ChiralBorane-BasedLewisAcidsforMetalFreeHydrogenations. . . 193
JanParadies
Index. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 217
vii
TopOrganometChem(2018)62:1–26
DOI:10.1007/3418_2015_141
#SpringerInternationalPublishingSwitzerland2015
Publishedonline:12August2015
The Future of Catalysis by Chiral Lewis
Acids
QiangSha,YongmingDeng,andMichaelP.Doyle
Abstract Even with the rapidly expanding popularity of organocatalysts for
organic reactions, chiral metal-based Lewis acid catalysts continue to have a
uniquely important role in asymmetric reactions. Their broad applicability to
cycloadditionandcondensationreactionsbasedoncloseencounteredassociations
ofLewisbasereactantswiththesechiralLewisacidcatalystsprovidesarchitectur-
allyconfinedcomplexesthatprovidehighstereocontrolintheirchemicalreactions.
Keywords Chiral ligands (cid:1) Condensation (cid:1) Cycloaddition (cid:1) Dipoles (cid:1)
Enantioselectivity(cid:1)Inhibition(cid:1)Transitionmetalcomplexes
Contents
1 Introduction................................................................................... 2
2 MetalComplexesasChiralLewisAcidCatalysts.......................................... 3
3 CycloadditionReactions..................................................................... 5
3.1 Diels–AlderReactions................................................................. 5
3.2 Hetero-Diels–AlderReactions......................................................... 7
3.3 DipolarCycloadditionReactions...................................................... 9
4 Carbonyl–EneReaction...................................................................... 15
Q.Sha
SchoolofChemicalEngineering,NanjingUniversityofScienceandTechnology,
Nanjing210094,People’sRepublicofChina
DepartmentofChemistry,TheUniversityofTexasatSanAntonio,SanAntonio,TX78230,
USA
Y.DengandM.P.Doyle(*)
DepartmentofChemistry,TheUniversityofTexasatSanAntonio,SanAntonio,TX78230,
USA
e-mail:[email protected]
2 Q.Shaetal.
5 CondensationReactions...................................................................... 17
5.1 AldolReactions........................................................................ 17
5.2 MannichReactions..................................................................... 18
5.3 MichaelReactions...................................................................... 18
5.4 Friedel–CraftsReactions............................................................... 20
References........................................................................................ 21
1 Introduction
AchiralLewisacidisacoordinativelyunsaturatedspeciesthatisnotsuperimpos-
able with its mirror image. With chiral ligand-associated complexes of aluminum
andboron,andmorecommonlyoftransitionmetalsthatincludecopper,palladium,
gold,iron,rhodium,silver,titanium,andzinc,theapplicationsofchiralLewisacids
as catalysts provide directional activation to a reactant intended to produce a
stereoisomeric product (Scheme 1). The outcome is usually enantiomeric enrich-
ment(withachiralreactants)ordiastereomericenrichment (withchiralreactants).
However,althoughthedevelopmentofeffectivechiralLewisacidsforasymmetric
catalysishas beenlongstanding,highstereocontrolinselectedreactionshasbeen
achievedonlyduringthepastquartercentury[1].
Acid catalysis is the driving force for the vast majority of organic chemical
reactions, and the reactions that are most susceptible to acid catalysis are those
whoserateisdependentonthepolarityofthesubstrate(s).Theacidthatisselected
operates as a proton donor (Brønsted acid) or an electron-pair acceptor (Lewis
acid), and the specific reaction dictates what the optimum choice will be.
This chapter will focus on Lewis acid catalysis to the exclusion of Brønsted acid
catalysis (organocatalysis) and will overview recent directions that point to the
future.TheadvantagesofLewisacidsincludetheirstructurallywell-definedligand
coordinationaroundthecentralmetal[2].Lewisacid-catalyzedreactionsconstitute
anenormityofchemicaltransformations,andtheyarewellreviewedinthisvolume
and elsewhere. This chapter is selective in its examples which are chosen to
illustrate the broad spectrum of applications by chiral Lewis acid catalysis with
focusonrecentdevelopmentsandcurrentchallenges.
Scheme1 CatalysisoforganicreactionsbychiralLewisacids