Catalyst-Controlled Switch in Diastereoselectivities: Enantioselective Construction of Functionalized 3,4-Dihydro-2H-thiopyrano[2,3-b]quinolines with Three Contiguous Stereocenters

Xin-Ni Ping; Pei-Shun Wei; Xiao-Qian Zhu; Jian-Wu Xie

doi:10.1021/acs.joc.6b02688

Catalyst-Controlled Switch in Diastereoselectivities: Enantioselective Construction of Functionalized 3,4-Dihydro-2H-thiopyrano[2,3-b]quinolines with Three Contiguous Stereocenters

J Org Chem. 2017 Feb 17;82(4):2205-2210. doi: 10.1021/acs.joc.6b02688. Epub 2017 Jan 30.

Authors

Xin-Ni Ping¹, Pei-Shun Wei¹, Xiao-Qian Zhu¹, Jian-Wu Xie¹

Affiliation

¹ Key Laboratory of the Ministry of Education for Advanced Catalysis Materials, Department of Chemistry and Life Science, Zhejiang Normal University , Jinhua 321004, P. R. China.

PMID: 28103439
DOI: 10.1021/acs.joc.6b02688

Abstract

A tandem Michael-Henry reaction of 2-mercaptoquinoline-3-carbaldehydes with nitroolefins using hydrogen-bonding-based cooperative organocatalysts for the highly diastereodivergent synthesis of chiral functionalized 3,4-dihydro-2H-thiopyrano[2,3-b]quinolines with three contiguous tertiary stereocenters has been developed.

Publication types

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