Lipase-catalyzed enantioselective ring opening of unactivated alicyclic-fused β-lactams in an organic solvent

被引：85

作者：

Forró, E ^{[1
]}

Fulöp, F ^{[1
]}

机构：

[1] Univ Szeged, Inst Pharmaceut Chem, H-6701 Szeged, Hungary

来源：

ORGANIC LETTERS | 2003年 / 5卷 / 08期

关键词：

D O I：

10.1021/ol034096o

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A highly efficient and very simple method was developed for the synthesis of enantiopure beta-amino acids (e.g. cispentacin) and beta-lactams through the enzyme-catalyzed enantioselective ring opening of unactivated alicyclic, beta-lactams in organic media. High enantioselectivity (E > 200) was observed when the Lipolase flipase B from Candida antarctica)-catalyzed reactions were performed with H2O (1 equiv) in dilsopropyl ether at 60 degreesC. The resolved products, obtained in good chemical yield (36-47%), could be easily separated.

引用

页码：1209 / 1212

页数：4

共 52 条

[51] Stereoselective synthesis of 3-substituted 2-aminocyclopentanecarboxylic acid derivatives and their incorporation into short 12-helical β-peptides that fold in water [J].

Woll, MG ;

Fisk, JD ;

LePlae, PR ;

Gellman, SH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (42) :12447-12452

[52] Nucleophilic openings of bicyclic β-lactones via acyl C-O and alkyl C-O cleavage:: catalytic, asymmetric synthesis of a versatile, carbocyclic nucleoside precursor and protected transpentacin [J].

Yokota, Y ;

Cortez, GS ;

Romo, D .

TETRAHEDRON, 2002, 58 (35) :7075-7080

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