Stereoselective Synthesis of Thiochromenes via Intramolecular Tandem Thio-Michael Addition of in Situ Generated alpha,beta-Unsaturated Aldehydes

作者:Kinfe Henok Hadgu*; Mebrahtu Fanuel Mesfin; Makolo Felix Loka; Moshapo Paseka Thendo; Manana Mandlenkosi Maxwell
来源:Journal of Organic Chemistry, 2014, 79(7): 3111-3118.
DOI:10.1021/jo5002164

摘要

An efficient and highly stereoselective strategy for the synthesis of 2,3-substituted thiochromenes having a complex and easily transformable group at the stereogenic center has been developed via a tandem thio-Michael addition reaction of an in situ generated alpha,beta-unsaturated aldehyde sugar derivative. The protocol is superior to reported protocols in that the carbohydrate-derived substituent at the stereogenic center of the thiochromene is versatile and is amenable for further transformation.

  • 出版日期2014-4-4