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

Authors

  • 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
Further Information

Publication History

Received: 25 November 2013

Accepted after revision: 17 January 2014

Publication Date:
06 March 2014 (online)


Graphical Abstract

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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