Intermolecular asymmetric carboesterification of alkenes by using chiral amine auxiliaries under O2: synthesis of enantioenriched α-methylene-γ-lactones through chloropalladation of alkynes

Chemistry : a European Journal
Zhenming ZhangHuanfeng Jiang

Abstract

Herein, the first example of chloropalladation-initiated asymmetric intermolecular carboesterification of alkenes with alkynes by using chiral amine auxiliaries is reported. The use of (1S,2S)-N(1),N(1)-dimethylcyclohexane-1,2-diamine auxiliaries is essential for providing α-methylene-γ-lactones products in moderate to high yields and excellent enantioselectivities at room temperature. Moreover, the chiral amine auxiliaries can be readily removed by hydrolysis during the reaction process to keep the absolute configuration. This oxygen- and water-promoted asymmetric reaction opens a new window to study asymmetric processes in halopalladation reactions.

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Citations

Jul 15, 2015·The Journal of Organic Chemistry·Zhenming ZhangJiawei Li
Jun 25, 2016·Chemical Reviews·David A PetroneMark Lautens
Jan 12, 2016·Chemical Communications : Chem Comm·Lihuan WuHuanfeng Jiang
Jun 18, 2017·Organic Letters·Jiuzhong HuangHuanfeng Jiang
May 7, 2015·Organic & Biomolecular Chemistry·Jianhui XiaAiwen Lei
Jan 9, 2016·Chemistry : a European Journal·Lucia CerisoliArianna Quintavalla
Oct 6, 2020·Angewandte Chemie·Sergio Cuesta-GalisteoCristina Nevado
Mar 4, 2017·Organic Letters·Jianhua LiaoHuanfeng Jiang

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