Synlett, Inhaltsverzeichnis Synlett 2014; 25(6): 876-880DOI: 10.1055/s-0033-1340817 letter © Georg Thieme Verlag Stuttgart · New YorkThio-Michael–Aldol–Cyclization Cascade of N-Enoyl Thiazolidinethiones with Aliphatic Aldehydes and Cyclic Ketones Authors Institutsangaben 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 Artikel empfehlen Abstract Artikel einzeln kaufen(opens in new window) Alle Artikel dieser Rubrik(opens in new window) 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. Key words Key wordsasymmetric synthesis - cascade reaction - chiral auxiliaries - thiazolidinethiones - Ti(IV) chloride Volltext Referenzen 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. Zusatzmaterial Zusatzmaterial Supporting Information (PDF) Primärdaten Primary Data (ZIP)
