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Double Diastereoselective Approach to Chiral syn- and anti-1,3-Diol Analogues through Consecutive Catalytic Asymmetric Borylations

Pujol, Alba; Whiting, Andrew

Double Diastereoselective Approach to Chiral syn- and anti-1,3-Diol Analogues through Consecutive Catalytic Asymmetric Borylations Thumbnail


Authors

Alba Pujol



Abstract

Homoallylic boronate carboxylate esters derived from unsaturated aldehydes via an imination, β-borylation, imine hydrolysis, and Wittig trapping sequence, were subjected to a second boryl addition to give 1,3-diborylated carboxylate esters. Control of the absolute and relative stereochemistry of the two new 1,3-stereogenic centers was achieved through: (1) direct chiral catalyst controlled asymmetric borylation of the first stereocenter on the unsaturated imine with high e.e.; and (2) a double diastereoselectively controlled borylation of an unsaturated ester employing a chiral catalyst to largely overcome directing effects from the first chiral boryl center to give poor (mismatched) to good (matched) diastereocontrol. Subsequently, the two C–B functions were transformed into C–O systems to allow unambiguous stereochemical assignment of the two borylation reactions involving oxidation and acetal formation.

Citation

Pujol, A., & Whiting, A. (2017). Double Diastereoselective Approach to Chiral syn- and anti-1,3-Diol Analogues through Consecutive Catalytic Asymmetric Borylations. Journal of Organic Chemistry, 82(14), 7265-7279. https://doi.org/10.1021/acs.joc.7b00854

Journal Article Type Article
Online Publication Date Jun 19, 2017
Publication Date Jun 19, 2017
Deposit Date Jul 7, 2017
Publicly Available Date Jun 19, 2018
Journal Journal of Organic Chemistry
Print ISSN 0022-3263
Electronic ISSN 1520-6904
Publisher American Chemical Society
Peer Reviewed Peer Reviewed
Volume 82
Issue 14
Pages 7265-7279
DOI https://doi.org/10.1021/acs.joc.7b00854

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Copyright Statement
This document is the Accepted Manuscript version of a Published Work that appeared in final form in The Journal of Organic Chemistry, copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see https://doi.org/10.1021/acs.joc.7b00854.







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