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

被引：37
|
作者：
Abraham, Elin [1 ]
Davies, Stephen G. [1 ]
Docherty, Alexander J. [1 ]
Ling, Kenneth B. [1 ]
Roberts, Paul M. [1 ]
Russell, Angela J. [1 ]
Thomson, James E. [1 ]
Toms, Steven M. [1 ]
机构：
[1] Univ Oxford, Chem Res Lab, Dept Chem, Oxford OX1 3TA, England
来源：
TETRAHEDRON-ASYMMETRY | 2008年 / 19卷 / 11期
关键词：
D O I：
10.1016/j.tetasy.2008.05.016
中图分类号：
O61 [无机化学];
学科分类号：
070301 ; 081704 ;
摘要：
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-(alpha-methylbenzyl)amide and lithium (R)N-3,4-dimethoxybenzyl-N-(alpha-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 (I R,2S,5S)- and (1S,2R,5R)-5-methyl-cispentacin in high yield, >98% de and >98% ee. (C) 2008 Elsevier Ltd. All rights reserved.
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页码：1356 / 1362
页数：7
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