Parallel kinetic resolution of methyl (RS)-5-tris(phenylthio)methyl-cyclopent-1-ene-carboxylate for the asymmetric synthesis of (1R,2S,5S)- and (1S,2R,5R)-5-methyl-cispentacin

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• 作者：Elin Abraham ; Stephen G. Davies ; Alex ; er J. Docherty ; Kenneth B. Ling ; Paul M. Roberts ; Angela J. Russell ; James E. Thomson ; Steven M. Toms
• 关键词：Microbicides ; Sexually transmitted infections ; Adolescents ; Research participation ; Ethics
• 刊名：Tetrahedron: Asymmetry
• 出版年：2008
• 出版时间：16 June 2008
• 年：2008
• 卷：19
• 期：11
• 页码：1356-1362
• 全文大小：322 K

文摘

Parallel kinetic resolution of methyl (RS)-5-tris(phenylthio)methyl-cyclopent-1-ene-carboxylate with a 50:50 pseudoenantiomeric mixture of lithium (S)-N-benzyl-N-(rc=""http://www.sciencedirect.com/scidirimg/entities/204e.gif"" alt=""greek small letter alpha"" title=""greek small letter alpha"" border=""0"">-methylbenzyl)amide and lithium (R)-N-3,4-dimethoxybenzyl-N-(rc=""http://www.sciencedirect.com/scidirimg/entities/204e.gif"" alt=""greek small letter alpha"" title=""greek small letter alpha"" border=""0"">-methylbenzyl)amide provides an efficient entry to the corresponding homochiral methyl (1R,2S,5S)- and (1S,2R,5R)-2-amino-5-tris(phenylthio)methyl-cyclopentane-carboxylate derivatives in >98 % de, with subsequent, sequential desulfurisation with Raney Nickel, N-debenzylation and ester hydrolysis furnishing (1R,2S,5S)- and (1S,2R,5R)-5-methyl-cispentacin in high yield, >98 % de and >98 % ee.