有机催化不对称 Morita-Baylis-Hillman 反应：靛红与乙烯砜的反应。

Organocatalytic Asymmetric Morita-Baylis-Hillman Reaction of Isatins with Vinyl Sulfones.

机构信息

Key Laboratory of Drug-Targeting and Drug Delivery System of the Ministry of Education and Sichuan Research Center for Drug Precision Industrial Technology, West China School of Pharmacy, Sichuan University, Chengdu 610041, China.

Engineering Center of Catalysis and Synthesis for Chiral Molecules, Department of Chemistry, Fudan University, Shanghai 200433, China.

出版信息

J Org Chem. 2023 Mar 17;88(6):3802-3807. doi: 10.1021/acs.joc.2c03073. Epub 2023 Feb 23.

DOI:10.1021/acs.joc.2c03073

PMID:36822154

Abstract

The organocatalytic asymmetric Morita-Baylis-Hillman (MBH) reaction of isatin derivatives with various vinyl sulfones is disclosed. Chiral sulfone-containing 3-hydroxyoxindoles were produced in good to high yields and with good to high ee's. This report displays an unprecedented example to apply activated alkenes with sulfone moiety other than carbonyl groups in asymmetric MBH reactions and provides an efficient strategy to incorporate the sulfone functional group for the synthesis of chiral 3-hydroxyoxindoles.

摘要

本文报道了手性亚砜基 3-羟基吲哚啉化合物的全新合成方法，该方法通过有机催化不对称 Morita-Baylis-Hillman（MBH）反应，以靛红衍生物与各种乙烯砜为原料，以较好到较高的产率和对映选择性得到目标产物。该反应首次应用含砜基而非羰基的活化烯烃作为亲偶极体参与不对称 MBH 反应，为在不对称 MBH 反应中引入砜基官能团提供了有效的策略。