Synlett, Table of Contents LETTER© Georg Thieme Verlag Stuttgart ˙ New YorkA Practical Synthesis of (S)-Cyclopent-2-enolMonica 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; Recommend Article Abstract Buy Article(opens in new window) All articles of this category(opens in new window) Corrected by: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 Full Text References References <A NAME="RG23909ST-1A">1a</A> Hildbrand S. Troxler T. Scheffold R. Helv. Chim. Acta 1994, 77: 1236 <A NAME="RG23909ST-1B">1b</A> Donohoe TJ. Moore PR. Waring MJ. Tetrahedron Lett. 1997, 38: 5027 <A NAME="RG23909ST-1C">1c</A> Goering BK. Ganem B. Tetrahedron Lett. 1994, 35: 6997 <A NAME="RG23909ST-2">2</A> Hu QY. Rege PD. Corey EJ. J. Am. Chem. Soc. 2004, 126: 5984 <A NAME="RG23909ST-3">3</A> Schinzer D. Bärmann H. Angew. Chem. Int. Ed. 1996, 35: 1678 <A NAME="RG23909ST-4A">4a</A> Huang L. Xue Z. The Alkaloids Vol. 23: Academic Press; New York: 1984. <A NAME="RG23909ST-4B">4b</A> Jalil Miah MA. Hudlicky T. Reed JW. The Alkaloids Vol. 51: Academic Press; New York: 1998. <A NAME="RG23909ST-5">5</A> Gonçalves-Martin MG. Ph.D. Thesis Universität Bern; Switzerland: 2007. <A NAME="RG23909ST-6A">6a</A> Wahhab A. Tavares DF. Rauk A. Can. J. Chem. 1990, 68: 1559 <A NAME="RG23909ST-6B">6b</A> Levina A. Muzart J. Tetrahedron: Asymmetry 1995, 6: 147 <A NAME="RG23909ST-6C">6c</A> Kitamura M. Kasahara I. Manabe K. Noyori R. Takaya H. J. Org. Chem. 1988, 53: 708 <A NAME="RG23909ST-6D">6d</A> Ito S. Kasai M. Ziffer H. Silverton JV. Can. J. Chem. 1987, 65: 574 <A NAME="RG23909ST-6E">6e</A> Hayashi T. Okamoto Y. Kabeta K. Hagihara T. Kumada M. J. Org. Chem. 1984, 49: 4224 <A NAME="RG23909ST-6F">6f</A> Gupta AK. Kazlauskas RJ. Tetrahedron: Asymmetry 1993, 4: 879 <A NAME="RG23909ST-7A">7a</A> Su H. Walder L. Zhang ZD. Scheffold R. Helv. Chim. Acta 1988, 71: 1073 <A NAME="RG23909ST-7B">7b</A> Bonhôte P. Scheffold R. Helv. Chim. Acta 1991, 74: 1425 <A NAME="RG23909ST-8">8</A> Bertilsson SK. Soedergren MJ. Andersson PG. J. Org. Chem. 2002, 67: 1567 <A NAME="RG23909ST-9A">9a</A> Gais H.-J. Bondarev O. Hetzer R. Tetrahedron Lett. 2005, 46: 6279 <A NAME="RG23909ST-9B">9b</A> Lüssem BJ. Gais H.-J. J. Am. Chem. Soc. 2003, 125: 6066 <A NAME="RG23909ST-9C">9c</A> Lüssem BJ. Gais H.-J. J. Org. Chem. 2004, 69: 4041 <A NAME="RG23909ST-10">10</A> Fukazawa T. Hashimoto T. Tetrahedron: Asymmetry 1993, 4: 2323 <A NAME="RG23909ST-11A">11a</A> Gokhale AS. Minidis ABE. Pfaltz A. Tetrahedron Lett. 1995, 36: 1831 <A NAME="RG23909ST-11B">11b</A> Andrus MB. Zhou Z. J. Am. Chem. Soc. 2002, 124: 8806 <A NAME="RG23909ST-11C">11c</A> Kawasaki K. Tsumura S. Katsuki T. Synlett 1995, 1245 <A NAME="RG23909ST-12">12</A> Matsumura K. Hashiguchi S. Ikariya T. Noyori R. J. Am. Chem. Soc. 1997, 119: 8738 <A NAME="RG23909ST-13">13</A> Kingsbury JS. Harrity JPA. Bonitatebus PJ. Hoveyda AH. J. Am. Chem. Soc. 1999, 121: 791 <A NAME="RG23909ST-14A">14a</A> Schwab P. France MB. Ziller JW. Grubbs RH. Angew. Chem. Int. Ed. 1995, 34: 2039 <A NAME="RG23909ST-14B">14b</A> Schwab P. Grubbs RH. Ziller JW. J. Am. Chem. Soc. 1996, 118: 100 <A NAME="RG23909ST-15">15</A> Saturnin C. Tabacchi R. Saxer A. Chimia 1993, 47: 221 Supplementary Material Supplementary Material Supporting Information (PDF)