Asymmetric Synthesis of Secondary and Tertiary Boronic Esters.

Angewandte Chemie
Beatrice S L CollinsVarinder K Aggarwal

Abstract

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.

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Citations

Aug 10, 2018·Angewandte Chemie·Jesse A MyhillJames P Morken
Sep 27, 2018·Angewandte Chemie·Jiefeng HuZhuangzhi Shi
Sep 4, 2018·Chemistry : a European Journal·Laura VillarAndrei V Malkov
Oct 30, 2018·Angewandte Chemie·Di WangZhuangzhi Shi
Mar 29, 2019·Dalton Transactions : an International Journal of Inorganic Chemistry·Qingxia YaoWenzeng Duan
May 9, 2019·Angewandte Chemie·Andrew J BochatJames M Takacs
Sep 19, 2019·Chemical Communications : Chem Comm·Yun-Shuai HuangYi-Feng Wang
Oct 16, 2019·Angewandte Chemie·Jingjing WuVarinder K Aggarwal
Jun 28, 2020·Angewandte Chemie·Hui WangVarinder Kumar Aggarwal
Aug 5, 2020·Chemical Communications : Chem Comm·Guobin MaHegui Gong
Jul 16, 2020·Chemistry : a European Journal·Santanu Panda, Kanak Kanti Das
Feb 5, 2019·Chemical Science·Jin-Jiang ZhangLi-Na Guo
May 5, 2020·Beilstein Journal of Organic Chemistry·Balaram S TakaleBruce H Lipshutz
Sep 2, 2020·Angewandte Chemie·Mitsutaka TakedaHirohisa Ohmiya
Sep 23, 2020·Chemistry : a European Journal·Jie Liu, Jan-E Bäckvall
Nov 5, 2020·Organic & Biomolecular Chemistry·Kanak Kanti DasSantanu Panda
Feb 6, 2021·Angewandte Chemie·Chang-Yun ShiLiang Yin
Apr 24, 2021·Organic & Biomolecular Chemistry·Keith SmithMark C Elliott
Jun 29, 2021·Journal of the American Chemical Society·Kai YangQiuling Song
Jun 25, 2021·Chemical Science·Yandong WangZhuangzhi Shi

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