Synlett 2014; 25(6): 876-880
DOI: 10.1055/s-0033-1340817
letter
© Georg Thieme Verlag Stuttgart · New York

Thio-Michael–Aldol–Cyclization Cascade of N-Enoyl Thiazolidinethiones with Aliphatic Aldehydes and Cyclic Ketones

Veronica M. Rivas
a   Medicinal and Natural Products Chemistry, The University of Iowa, Iowa City, IA 52242, USA   Fax: +1(319)3358766   Email: horacio-olivo@uiowa.edu
b   Departamento de Química Analítica, Facultad de Medicina, Universidad Autónoma de Nuevo León, Monterrey, N.L. 64841, México
,
Laura Munive
a   Medicinal and Natural Products Chemistry, The University of Iowa, Iowa City, IA 52242, USA   Fax: +1(319)3358766   Email: horacio-olivo@uiowa.edu
c   Facultad de Ciencias Químicas, Benemérita Universidad Autónoma de Puebla, Puebla 72570, México
,
Horacio F. Olivo*
a   Medicinal and Natural Products Chemistry, The University of Iowa, Iowa City, IA 52242, USA   Fax: +1(319)3358766   Email: horacio-olivo@uiowa.edu
› Author Affiliations
Further Information

Publication History

Received: 25 November 2013

Accepted after revision: 17 January 2014

Publication Date:
06 March 2014 (online)


Abstract

A thio-Michael–aldol–cyclization cascade reaction of N-enoyl thiazolidinethiones with aliphatic aldehydes and cyclic ­ketones was promoted by Ti(IV) chloride to deliver highly complex tricyclic adducts possessing a carbon atom tetrasubstituted with ­heteroatoms and up to four stereogenic centers in good to very good yields.

Supporting Information

Primary Data