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

 
  • References and Notes

    • 1a Nicolaou KC, Edmonds DJ, Bulger PG. Angew. Chem. Int. Ed. 2006; 45: 7134
    • 1b Alba AN, Companyo X, Viciano M, Rios R. Curr. Org. Chem. 2009; 13: 1432
    • 1c Tietze L. Chem. Rev. 1996; 96: 115
    • 1d D’Souza DM, Müller TJ. J. Chem. Soc. Rev. 2007; 36: 1095
    • 1e Wasilke J.-C, Obrey SJ, Baker RT, Bazan GC. Chem. Rev. 2005; 105: 1001
    • 2a Velazquez F, Olivo HF. Curr. Org. Chem. 2002; 6: 303
    • 2b Ortiz A, Sansinenea E. J. Sulfur Chem. 2007; 28: 109
  • 3 Sabala R, Hernandez-Garcia L, Ortiz A, Romero M, Olivo HF. Org. Lett. 2010; 12: 4268
  • 4 Munive L, Rivas VM, Ortiz A, Olivo HF. Org. Lett. 2012; 14: 3514
    • 5a Palomo C, Oiarbide M, Dias F, Ortiz A, Linden A. J. Am. Chem. Soc. 2001; 123: 5602
    • 5b Ortiz A, Quintero L, Hernández H, Maldonado S, Mendoza G, Bernes S. Tetrahedron Lett. 2003; 44: 1129
    • 5c Palomo C, Oiarbide M, Dias F, López R, Linden A. Angew. Chem. Int. Ed. 2004; 43: 3307
    • 5d Palomo C, Oiarbide M, Lopez R, Gonzalez PB, Gomez-Bengoa E, Saa JM, Linden A. J. Am. Chem. Soc. 2006; 128: 15236
  • 6 Davies SG, Hermann GJ, Sweet MJ, Smith AD. Chem. Commun. 2004; 1128
  • 7 See, for example: CCDC-980430 and CCDC-980714 (Figure 2). This data can be obtained free of charge from the Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk.
    • 8a Kataoka T, Kinoshita H, Kinoshita S, Osamura T, Watanabe S.-i, Iwamura T, Muraoka O, Tanabe G. Angew. Chem. Int. Ed. 2003; 42: 2889
    • 8b Kataoka T, Hinoshita H. Eur. J. Org. Chem. 2005; 45
    • 8c Kinoshita H, Osamura T, Mizuno K, Kinoshita S, Iwamura T, Watanabe S.-i, Kataoka T, Muraoka O, Tanabe G. Chem. Eur. J. 2006; 12: 3896
  • 9 Osorio-Lozada A, Olivo HF. Org. Lett. 2008; 10: 617
  • 10 CCDC-972601 contains the supplementary crystallographic data for compound 7. This data can be obtained free of charge from the Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk.