Nucleophilic additions of Grignard reagents to N-benzyl-2,3-O-isopropylidene-D-glyceraldehyde nitrone (BIGN).: Synthesis of (2S,3R) and (2S,3S)-3-phenylisoserine.

被引:46
作者
Merino, P [1 ]
Castillo, E [1 ]
Franco, S [1 ]
Merchán, FL [1 ]
Tejero, T [1 ]
机构
[1] Univ Zaragoza, CSIC, ICMA, Fac Ciencias,Dept Quim Organ, Zaragoza, Aragon, Spain
关键词
nitrones; hydroxylamines; hydroxy acids and derivatives; amino alcohols;
D O I
10.1016/S0040-4020(98)00741-8
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A remarkable Lewis acid tuning has been observed in the nucleophilic addition of Grignard reagent to BIGN, the N-benzyl nitrone derived from 1,2-O-isopropylidene-D-glyceraldehyde. The obtained alpha,beta-dialkoxy hydroxylamines can serve as starting points for the synthesis of both aminodiols and alpha-hydroxy-beta-amino acids. This synthetic approach is illustrated by the synthesis of the antipode of the C-13 side chain of Taxotere as well as its C-3 epimer. (C) 1998 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:12301 / 12322
页数:22
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