Organocatalytic One-Pot Asymmetric Synthesis of Thiolated Spiro-γ-lactam Oxindoles Bearing Three Stereocenters

Xin Huang; Miao Liu; Kenny Pham; Xiaofeng Zhang; Wen-Bin Yi; Jerry P Jasinski; Wei Zhang

doi:10.1021/acs.joc.6b00653

Organocatalytic One-Pot Asymmetric Synthesis of Thiolated Spiro-γ-lactam Oxindoles Bearing Three Stereocenters

J Org Chem. 2016 Jul 1;81(13):5362-9. doi: 10.1021/acs.joc.6b00653. Epub 2016 Jun 14.

Authors

Xin Huang¹, Miao Liu¹, Kenny Pham¹, Xiaofeng Zhang¹, Wen-Bin Yi², Jerry P Jasinski³, Wei Zhang¹

Affiliations

¹ Department of Chemistry, University of Massachusetts , 100 Morrissey Boulevard, Boston, Massachusetts 02125, United States.
² School of Chemical Engineering, Nanjing University of Science and Technology , Nanjing 210094, China.
³ Department of Chemistry, Keene State College , Keene, New Hampshire 03435-2001, United States.

PMID: 27258150
DOI: 10.1021/acs.joc.6b00653

Abstract

The first asymmetric synthesis of spiro-γ-lactam oxindoles bearing three stereocenters is reported. One-pot thiol-Michael/Mannich/lactamization reactions promoted by a recyclable fluorous bifunctional cinchona alkaloid/thiourea organocatalyst afford products in moderate to good yields with up to 95% ee and 6:1 dr.

Publication types

Research Support, U.S. Gov't, Non-P.H.S.