Enantioselective organocatalytic domino Michael/aldol reactions: an efficient procedure for the stereocontrolled construction of 2H-thiopyrano[2,3-b]quinoline scaffolds

Lulu Wu; Youming Wang; Haibin Song; Liangfu Tang; Zhenghong Zhou; Chuchi Tang

doi:10.1002/asia.201300450

Enantioselective organocatalytic domino Michael/aldol reactions: an efficient procedure for the stereocontrolled construction of 2H-thiopyrano[2,3-b]quinoline scaffolds

Chem Asian J. 2013 Sep;8(9):2204-10. doi: 10.1002/asia.201300450. Epub 2013 May 31.

Authors

Lulu Wu¹, Youming Wang, Haibin Song, Liangfu Tang, Zhenghong Zhou, Chuchi Tang

Affiliation

¹ Institute and State Key Laboratory of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, PR China.

PMID: 23728825
DOI: 10.1002/asia.201300450

Abstract

An efficient procedure for the stereocontrolled construction of 2H-thiopyrano[2,3-b]quinoline scaffolds has been developed, starting from simple compounds. The domino Michael/aldol reactions between 2-mercaptobenzaldehydes and enals, promoted by chiral diphenylprolinol TMS ether, proceed with excellent chemo- and enantioselectivity to give the corresponding synthetically useful and pharmaceutically valuable 2H-thiopyrano[2,3-b]quinolines in high yields with 90-99 % ee.

Keywords: Michael addition; aldol reaction; enals; heterocycles; organocatalysis.