Synthesis of pyrrolizidine derivatives by 1,3-dipolar cycloaddition reactions of chiral five-membered cyclic azomethine ylides

被引：11
作者：
Argyropoulos, Nikolaos G. [1 ]
Sarli, Vasiliki C.
Gdaniec, Maria
机构：
[1] Univ Thessaloniki, Dept Chem, Thessaloniki 54124, Greece
[2] Adam Mickiewicz Univ, Fac Chem, PL-60780 Poznan, Poland
来源：
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2006年 / 2006卷 / 16期
关键词：
cycloaddition; pyrrolizidine; ylides; regioselectivity;
D O I：
10.1002/ejoc.200600207
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The 1,3-dipolar cycloaddition reactions of chiral five-membered cyclic azomethine ylides, generated in situ from ethyl glyoxylate and protected (3S,4S)-dihydroxypyrrolidines 3 and 6 have been studied, The facial selectivity of the cycloaddition reaction is governed by the steric effect of the substituent on the pyrrolidine ring next to the azomethine ylide functionality, leading in all cases to an exclusive Si face approach of the dipolarophile. The exo/endo selectivity depends on the dipolarophile and on the size of the other substituent on the pyrrolidine ring. ((c) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)
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收藏
页码：3738 / 3745
页数：8
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