Enantiodivergent synthesis of 2-hydroxymethyl-3-hydroxy-4-nitro-pyrrolidines through tandem Michael-Henry reaction using L-serine as the chiral educt.

被引:29
作者
Barco, A [1 ]
Benetti, S [1 ]
DeRisi, C [1 ]
Pollini, GP [1 ]
Romagnoli, R [1 ]
Zanirato, V [1 ]
机构
[1] DIPARTIMENTO SCI FARMACEUT,I-44100 FERRARA,ITALY
关键词
D O I
10.1016/0040-4039(96)01671-1
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
By utilizing L-serine, both enantiomers of all trans a-hydroxymethyl 3-hydroxy-4-nitro-pyrrolidine were efficiently prepared through tandem Michael-Henry methodology. Their stereochemistry has been assigned through conversion of one of them to trans 2-hydroxymethyl-3-hydroxypyrrolidine, a naturally occurring compound recently isolated from Castanospermum australe. Copyright (C) 1996 Elsevier Science Ltd
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页码:7599 / 7602
页数:4
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