A STRAIGHTFORWARD SYNTHESIS OF (PLUS-OR-MINUS)-4-AMINO-4-DEOXYERYTHROSE VIA ITS BISULFITE ANOMER

被引：0
|
作者：
BEHR, JB
DEFOIN, A
STREITH, J
机构：
来源：
HETEROCYCLES | 1994年 / 37卷 / 02期
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D O I：
暂无
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Hetero-Diels-Alder reaction of N-butadienyl-2-pyrrolidone (1a) with acylnitroso dienophile (3) led with very high regioselectivity to the racemic cycloadduct (6). A sequence of stereospecific reactions, as well as some protection/deprotection steps, gave the bisulfite derivative (2b) of (+/-)-4-amino-4-deoxyerythrose (2a) as a single and crystalline anomer. Asymmetric induction as applied to the Diels-Alder cycloaddition step with various N-butadienylpyroglutamate esters (1b-e) permitted to work out optimal experimental conditions, the best d.e. value being 76%.
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页码：747 / 750
页数：4
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