New enantiodivergent procedure for the syntheses of chiral α-substituted serines from α-alkyl-α-aminomalonates utilizing enzymatic hydrolysis

被引:33
作者
Sano, S [1 ]
Hayashi, K [1 ]
Miwa, T [1 ]
Ishii, T [1 ]
Fujii, M [1 ]
Mima, H [1 ]
Nagao, Y [1 ]
机构
[1] Univ Tokushima, Fac Pharmaceut Sci, Tokushima 7708505, Japan
关键词
amino acids and derivatives; asymmetric synthesis; enzymes and enzyme reactions; reduction;
D O I
10.1016/S0040-4039(98)01123-X
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Porcine liver eaterase (PLE)- or rabbit liver eaterase (RLE)-catalyzed hydrolysis of the pro-S eater group of diethyl alpha-alkyl-alpha -(benzyloxycarbonylamino)malonate s 2a-e afforded (R)-ethyl alpha-alkyl-alpha -(benzyloxycarbonylamino)malonates 3a-e each in excellent enantiomeric excess. Enantiodivergent reductions of these acid eaters 3a-e readily furnished both the corresponding enantiomeric alpha-substituted serines (R)- and (S)-5a-c. (C) 1998 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:5571 / 5574
页数:4
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