Vicinal All‐Carbon Quaternary Stereocenter Construction with Trifluoromethyl Groups via Organocatalytic Asymmetric Cascade Michael/Michael Reaction

Author:

Tsuyusaki Ryo1,Nakashima Kosuke1,Matsushima Yasuyuki1,Hirashima Shin‐ichi1,Miura Tsuyoshi1ORCID

Affiliation:

1. School of Pharmacy Tokyo University of Pharmacy and Life Sciences 1432-1 Horinouchi Hachioji Tokyo 192-0392 Japan

Abstract

AbstractA thiourea organocatalyst efficiently promoted the asymmetric cascade Michael/Michael reactions between isatin‐derived trifluoromethylacrylate and α‐alkylidene succinimide, resulting in high yields of spirooxindole derivatives. These compounds exhibit vicinal all‐carbon quaternary stereocenters and bear a trifluoromethyl group, with excellent enantioselectivities reaching up to 99 % ee. This work represents the first successful organocatalyst application for the direct construction of vicinal all‐carbon quaternary stereocenters, featuring a trifluoromethyl group.

Publisher

Wiley

Subject

General Chemistry,Biochemistry,Organic Chemistry

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