Reversible 1,3-anti/syn-stereochemical courses in copper-catalyzed γ-selective allyl-alkyl coupling between chiral allylic phosphates and alkylboranes

Journal of the American Chemical Society
Kazunori NagaoMasaya Sawamura

Abstract

The stereochemical courses of the copper-catalyzed allyl-alkyl coupling between enantioenriched chiral allylic phosphates and alkylboranes were switchable between 1,3-anti and 1,3-syn selectivities by the choice of solvents and achiral alkoxide bases with different steric demands. The reactions with γ-silylated allylic phosphates allow efficient synthesis of enantioenriched chiral allylsilanes with tertiary or quaternary carbon stereogenic centers. Cyclic and acyclic bimodal participation of alkoxyborane species in an organocopper addition-elimination sequence is proposed to account for the phenomenon of the anti/syn-stereochemical reversal.

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Citations

Sep 10, 2016·Journal of the American Chemical Society·Qi ZhouMary P Watson
Nov 4, 2016·Journal of the American Chemical Society·Jung Tae HanJaesook Yun
Jul 18, 2014·Journal of the American Chemical Society·Kazunori NagaoMasaya Sawamura
Dec 6, 2014·Angewandte Chemie·Nootaree NiljianskulStephen L Buchwald
Jul 6, 2014·Angewandte Chemie·Kazuhiko SembaYasushi Tsuji
Oct 5, 2018·Chemical Communications : Chem Comm·Sarah M Pound, Mary P Watson
Jan 7, 2016·Beilstein Journal of Organic Chemistry·Takamichi WakamatsuMasaya Sawamura
Oct 19, 2016·Chemical Record : an Official Publication of the Chemical Society of Japan ... [et Al.]·Yasushi Tsuji, Tetsuaki Fujihara
May 28, 2015·Chemistry : a European Journal·Yuto YasudaMasaya Sawamura
Jul 4, 2012·Journal of the American Chemical Society·Mika YoshidaMasaya Sawamura
Oct 31, 2012·Journal of the American Chemical Society·Yoshinori ShidoMasaya Sawamura

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