D-Allal- and D-Galactal-Derived Vinyl N-Mesylaziridines: Regio- and Stereoselectivity in Addition Reactions of O-, C-, N-, and S-Nucleophiles

被引：7
|
作者：
Di Bussolo, Valeria [1 ]
Frau, Ileana [1 ]
Pineschi, Mauro [1 ]
Crotti, Paolo [1 ]
机构：
[1] Univ Pisa, Dipartimento Sci Farmaceut, I-56126 Pisa, Italy
来源：
SYNTHESIS-STUTTGART | 2012年 / 44卷 / 18期
关键词：
glycosylations; regioselectivity; stereoselectivity; nucleophilic additions; heterocycles; OXIRANE; REGIOSELECTIVITY; GLYCOSYLATION; GLYCOSIDATION; STRATEGY; SUGARS; AZIDE;
D O I：
10.1055/s-0031-1291137
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The regioselectivity and stereoselectivity were examined of the addition reactions of O-, C-, N-and S-nucleophiles to D-allal- and D-galactal-derived N-mesylaziridines. The ratio of 1,4-regioselectivity (exclusive syn-1,4-addition) to 1,2-regioselectivity (exclusive anti-1,2-addition) was strictly and directly dependent on the ability of the nucleophile to coordinate with the nitrogen atom of the aziridine.
引用
收藏
页码：2863 / 2871
页数：9
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