Enantioselective cobalt-catalysed transformations

240 Pages·2018·17.243 MB·English

by  Pellissier, Hélène

Enantioselective Cobalt-catalysed Transformations
Catalysis Series
Series editors:
Bert Klein Gebbink, Utrecht University, The Netherlands
Jose Rodriguez, Brookhaven National Laboratory, USA
Titles in the series:
1: Carbons and Carbon Supported Catalysts in Hydroprocessing
2: Chiral Sulfur Ligands: Asymmetric Catalysis
3: Recent Developments in Asymmetric Organocatalysis
4: Catalysis in the Refining of Fischer–Tropsch Syncrude
5: O rganocatalytic Enantioselective Conjugate Addition Reactions:
A Powerful Tool for the Stereocontrolled Synthesis of Complex Molecules
6: N-Heterocyclic Carbenes: From Laboratory Curiosities to Efficient Syn-
thetic Tools
7: P-Stereogenic Ligands in Enantioselective Catalysis
8: Chemistry of the Morita–Baylis–Hillman Reaction
9: Proton-Coupled Electron Transfer: A Carrefour of Chemical Reactivity
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10: Asymmetric Domino Reactions
11: C–H and C-X Bond Functionalization: Transition Metal Mediation
12: Metal Organic Frameworks as Heterogeneous Catalysts
13: Environmental Catalysis Over Gold-Based Materials
14: Computational Catalysis
15: Catalysis in Ionic Liquids: From Catalyst Synthesis to Application
16: Economic Synthesis of Heterocycles: Zinc, Iron, Copper, Cobalt,
Manganese and Nickel Catalysts
17: Metal Nanoparticles for Catalysis: Advances and Applications
18: Heterogeneous Gold Catalysts and Catalysis
19: Conjugated Linoleic Acids and Conjugated Vegetable Oils
20: Enantioselective Multicatalysed Tandem Reactions
21: New Trends in Cross-Coupling: Theory and Applications
22: Atomically-Precise Methods for Synthesis of Solid Catalysts
23: Nanostructured Carbon Materials for Catalysis
24: Heterocycles from Double-Functionalized Arenes: Transition Metal
Catalyzed Coupling Reactions
25: Asymmetric Functionalization of C–H Bonds
26: Enantioselective Nickel-catalysed Transformations
27: N-Heterocyclic Carbenes: From Laboratory Curiosities to Efficient
Synthetic Tools, 2nd edition
28: Zeolites in Catalysis: Properties and Applications
29: Biocatalysis: An Industrial Perspective
30: Dienamine Catalysis for Organic Synthesis
31: Metal-free Functionalized Carbons in Catalysis: Synthesis, Characteriza-
tion and Applications
32: Modern Biocatalysis: Advances Towards Synthetic Biological Systems
33: NO Trap Catalysts and Technologies: Fundamentals and Industrial
x
Applications
34: Alternative Catalytic Materials: Carbides, Nitrides, Phosphides and
Amorphous Boron Alloys
35: Enantioselective Cobalt-catalysed Transformations
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Enantioselective Cobalt-
catalysed Transformations
By
Hélène Pellissier
CNRS, France
Email: [email protected]
Catalysis Series No. 35
Print ISBN: 978-1-78801-462-5
PDF ISBN: 978-1-78801-509-7
EPUB ISBN: 978-1-78801-515-8
Print ISSN: 1757-6725
Electronic ISSN: 1757-6733
A catalogue record for this book is available from the British Library
© Hélène Pellissier 2018
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Foreword
The science of synthesis has transformed our world and opened a gateway
to a molecular universe filled with previously unimaginable opportunities.
Our improving ability to make molecules has profoundly changed how we
think about nature's chemome, enabling access to natural materials often of
otherwise limited availability and at the same time providing new structures
with improved or totally new functions. Our significantly advanced ability to
make molecules has now also placed emphasis on which molecules to make
and the importance of achieving function through synthesis-informed design
(function oriented synthesis). Collectively, these advances have enhanced
our understanding of chemistry and in so doing they have significantly and
beneficially impacted research, medicine, materials science, energy, environ-
mental stewardship, our economy and our quality of life. Synthetic access
to molecules and thus molecular function has more generally opened new
frontiers in all of science from molecular anthropology to molecular zoology
and all disciplines in between.
The reach of synthesis relies on and is inexorably determined by the dis-
covery and invention of new reactivities and reactions. This is clearly evi-
dent from the number of molecules once considered impossible to make
that are now often routinely and step-economically prepared through the
creative use of our ever-expanding reaction lexicon. While tracing its roots to
the 18th century, organometallic chemistry and especially transition metal
chemistry have figured significantly in advancing our molecule-making
expertise. By modulating pi and sigma bond reactivities, transition metals
in particular have changed how we think about bond formation. The once
limited and historically recognized reactivity of functional groups, for exam-
ple, has now been changed and vastly expanded as their reactivities are often
enhanced or totally changed by interactions with transition metals. Vast

Catalysis Series No. 35
Enantioselective Cobalt-catalysed Transformations
By Hélène Pellissier
© Hélène Pellissier 2018
Published by the Royal Society of Chemistry, www.rsc.org
vii
viii Foreword
new opportunities and choices are now made possible for green chemistry,
improving step economy and bringing molecular construction closer to the
ideal synthesis.
In this book, Hélène Pellissier, who has authored numerous noteworthy
contributions to reaction science, provides an impressively comprehensive
and insightful overview of enantioselective cobalt-catalyzed transforma-
tions. Building on her scholarly review (Chemical Reviews 2014) of the field
a few years ago, this considerably updated and expanded analysis serves as
a superb survey of the remarkable reach of cobalt-catalyzed transformations
and the many and varied strategies to control their absolute stereochemical
outcome. From cobalt-catalyzed cycloadditions and cyclizations to reduc-
tions, condensations, coupling reactions, epoxide ring opening and oligo-
merizations and beyond, this tome captures the richness of organocobalt
chemistry and its increasing impact on stereocontrolled synthesis. It is at
once a celebration and recognition of the impressive achievements of those
in the cobalt chemistry field and a forerunner of things to come.
The structure of each chapter in this book commendably provides a brief
historical perspective and an information-rich summary of contemporary
progress punctuated by representative contributions, mechanistic analyses,
and insightful conclusions. The graphical presentations are superbly to the
point, adding to the readability of this work. This book also benefits greatly
from its perspective as well as its up-to-date nature, serving as a “must read”
for those in the field as well as for those interested in emerging trends in
organometallic chemistry. It is noteworthy and reflective of the growth of the
field that not too many years ago, the field of organometallic chemistry was
ambitiously addressed by some in single books. Now even enantioselective
transformations of cobalt could fill many.
Like other transition metals, cobalt-based reagents and catalysts have had
and continue to have a striking impact on the practice of synthesis and on
our understanding of molecular reactivity. This book is a snapshot of the
state of the science and a comprehensive collection of cobalt based reactions.
It serves at the same time as a reference point and inspirational foundation
for future advances in the field. Cobalt chemistry and more generally, metal
catalysis, are shaping our approach to synthesis and with that the beneficial
impact of synthesis on science and society.
Paul A. Wender
Bergstrom Professor of Chemistry
Stanford University
Abbreviations
Acac Acetylacetone
Ar Aryl
BDPP 2,4-Bis(diphenylphosphino)pentane
BINAP 2,2′-Bis(diphenylphosphino)-1,1′-binaphthyl
BINOL 1,1′-Bi-2-naphthol
BIPHEP 2,2′-Bis(diphenylphosphino)-1,1′-biphenyl
Bn Benzyl
Boc Tert-butoxycarbonyl
BOPA Bis(oxazolinylphenyl)amine
BTFEP 1,3-Bis(2,2,2-trifluoroethoxy)propan-2-ol
Bz Benzoyl
CAN Ceric ammonium nitrate
Cbz Benzyloxycarbonyl
CHIRAPHOS 2,3-Bis(diphenylphosphine)butane
Cod Cyclooctadiene
Cy Cyclohexyl
DBFOX 4,6-Dibenzofurandiyl-2,2′-bis-(4-phenyloxazoline)
DBU 1,8-Diazabicyclo[5.4.0]undec-7-ene
DCE 1,2-Dichloroethane
de diastereomeric excess
DIOP 2,3-O-isopropylidene-2,3-dihydroxy-1,4-bis-(diphenylphosphino)
butane
DIPAMP 1,2-[(2-Methoxyphenyl)phenylphosphino]ethane
DIPEA Diisopropylethylamine
DMAP 4-(N,N′-Dimethylamino)pyridine
DME Dimethoxyethane
DMF Dimethylformamide
DMSO Dimethylsulfoxide

Catalysis Series No. 35
Enantioselective Cobalt-catalysed Transformations
By Hélène Pellissier
© Hélène Pellissier 2018
Published by the Royal Society of Chemistry, www.rsc.org
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