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.

引用

页码：1356 / 1362

页数：7

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