Synlett, Inhaltsverzeichnis LETTER © Georg Thieme Verlag Stuttgart ˙ New York A Practical Synthesis of (S)-Cyclopent-2-enol Monica G. Gonçalves-Martin, Andreas Saxer, Philippe Renaud*Departement für Chemie und Biochemie, Universität Bern, Freiestr. 3, 3012 Bern, SwitzerlandFax: +41(31)6313426; e-Mail: philippe.renaud@ioc.unibe.ch; Artikel empfehlen Abstract Artikel einzeln kaufen Alle Artikel dieser Rubrik Erratum zu diesem Artikel: A Practical Synthesis of (S)-Cyclopent-2-enolSynlett 2010; 2010(05): 840-840DOI: 10.1055/s-0029-1219555 Abstract An efficient and scalable procedure for the synthesis of (S)-cyclopent-2-enol is reported. The two key steps of the synthesis are the Noyori’s Ru-catalyzed transfer hydrogenation of an ynone and ring-closing metathesis of a 1,6-heptadiene. Key words asymmetric synthesis - transfer hydrogenation - ring-closing metathesis - allylic alcohol Volltext Referenzen References 1a Hildbrand S. Troxler T. Scheffold R. Helv. Chim. Acta 1994, 77: 1236 1b Donohoe TJ. Moore PR. Waring MJ. Tetrahedron Lett. 1997, 38: 5027 1c Goering BK. Ganem B. Tetrahedron Lett. 1994, 35: 6997 2 Hu QY. Rege PD. Corey EJ. J. Am. Chem. Soc. 2004, 126: 5984 3 Schinzer D. Bärmann H. Angew. Chem. Int. Ed. 1996, 35: 1678 4a Huang L. Xue Z. The Alkaloids Vol. 23: Academic Press; New York: 1984. 4b Jalil Miah MA. Hudlicky T. Reed JW. The Alkaloids Vol. 51: Academic Press; New York: 1998. 5 Gonçalves-Martin MG. Ph.D. Thesis Universität Bern; Switzerland: 2007. 6a Wahhab A. Tavares DF. Rauk A. Can. J. Chem. 1990, 68: 1559 6b Levina A. Muzart J. Tetrahedron: Asymmetry 1995, 6: 147 6c Kitamura M. Kasahara I. Manabe K. Noyori R. Takaya H. J. Org. Chem. 1988, 53: 708 6d Ito S. Kasai M. Ziffer H. Silverton JV. Can. J. Chem. 1987, 65: 574 6e Hayashi T. Okamoto Y. Kabeta K. Hagihara T. Kumada M. J. Org. Chem. 1984, 49: 4224 6f Gupta AK. Kazlauskas RJ. Tetrahedron: Asymmetry 1993, 4: 879 7a Su H. Walder L. Zhang ZD. Scheffold R. Helv. Chim. Acta 1988, 71: 1073 7b Bonhôte P. Scheffold R. Helv. Chim. Acta 1991, 74: 1425 8 Bertilsson SK. Soedergren MJ. Andersson PG. J. Org. Chem. 2002, 67: 1567 9a Gais H.-J. Bondarev O. Hetzer R. Tetrahedron Lett. 2005, 46: 6279 9b Lüssem BJ. Gais H.-J. J. Am. Chem. Soc. 2003, 125: 6066 9c Lüssem BJ. Gais H.-J. J. Org. Chem. 2004, 69: 4041 10 Fukazawa T. Hashimoto T. Tetrahedron: Asymmetry 1993, 4: 2323 11a Gokhale AS. Minidis ABE. Pfaltz A. Tetrahedron Lett. 1995, 36: 1831 11b Andrus MB. Zhou Z. J. Am. Chem. Soc. 2002, 124: 8806 11c Kawasaki K. Tsumura S. Katsuki T. Synlett 1995, 1245 12 Matsumura K. Hashiguchi S. Ikariya T. Noyori R. J. Am. Chem. Soc. 1997, 119: 8738 13 Kingsbury JS. Harrity JPA. Bonitatebus PJ. Hoveyda AH. J. Am. Chem. Soc. 1999, 121: 791 14a Schwab P. France MB. Ziller JW. Grubbs RH. Angew. Chem. Int. Ed. 1995, 34: 2039 14b Schwab P. Grubbs RH. Ziller JW. J. Am. Chem. Soc. 1996, 118: 100 15 Saturnin C. Tabacchi R. Saxer A. Chimia 1993, 47: 221 Zusatzmaterial Zusatzmaterial Supporting Information
