Asymmetric Synthesis of Secondary and Tertiary Boronic Esters

Non‐racemic chiral boronic esters are recognised as immensely valuable building blocks in modern organic synthesis. Their stereospecific transformation into a variety of functional groups—from amines and halides to arenes and alkynes—along with their air and moisture stability, has established them...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2017-09, Vol.56 (39), p.11700-11733
Main Authors: Collins, Beatrice S. L., Wilson, Claire M., Myers, Eddie L., Aggarwal, Varinder K.
Format: Article
Language:English
Subjects:
Alkynes
Amines
Aromatic compounds
Asymmetric synthesis
Asymmetry
Boron
boronic esters
Esters
Functional groups
Halides
Hydroboration
Modularity
Synthesis
synthetic methods
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Summary:Non‐racemic chiral boronic esters are recognised as immensely valuable building blocks in modern organic synthesis. Their stereospecific transformation into a variety of functional groups—from amines and halides to arenes and alkynes—along with their air and moisture stability, has established them as an important target for asymmetric synthesis. Efforts towards the stereoselective synthesis of secondary and tertiary alkyl boronic esters have spanned over five decades and are underpinned by a wealth of reactivity platforms, drawing on the unique and varied reactivity of boron. This Review summarizes strategies for the asymmetric synthesis of alkyl boronic esters, from the seminal hydroboration methods of H. C. Brown to the current state of the art. Non‐racemic chiral boronic esters are immensely valuable building blocks in modern organic synthesis. Their stereospecific transformation into a variety of functional groups, along with their air and moisture stability, has established them as an important target for asymmetric synthesis. Methods for their asymmetric synthesis now span a wealth of reactivity platforms.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201701963