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Asymmetric Synthesis of Secondary and Tertiary Boronic Esters
Author(s) -
Collins Beatrice S. L.,
Wilson Claire M.,
Myers Eddie L.,
Aggarwal Varinder K.
Publication year - 2017
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201701963
Subject(s) - hydroboration , alkyl , chemistry , reactivity (psychology) , stereoselectivity , stereospecificity , organic chemistry , organic synthesis , suzuki reaction , halide , boronic acid , combinatorial chemistry , catalysis , aryl , medicine , alternative medicine , pathology
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.