Rapid and stereocontrolled synthesis of racemic and optically pure highly functionalized pyrrolizidine systems via rearrangement of 1,3-dipolar cycloadducts derived from 2-azetidinone-tethered azomethine ylides

被引:50
作者
Alcaide, B [1 ]
Almendros, P
Alonso, JM
Aly, MF
机构
[1] Univ Complutense Madrid, Fac Quim, Dept Quim Organ 1, E-28040 Madrid, Spain
[2] S Valley Univ, Fac Sci, Dept Chem, Qena, Egypt
关键词
D O I
10.1021/jo005686s
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
This work describes a convenient procedure for the straightforward preparation of polyfunctionalized enantiopure pyrrolizidine systems. The methodology capitalizes on a HCl(g)-promoted reaction of the 1,3-dipolar cycloadducts derived from 2-azetidinone-tethered azomethine ylides, smoothly affording different types of highly functionalized bi- and tricyclic systems in racemic and optically pure forms. This process involves a selective bond cleavage of the four-membered ring, followed by a rearrangement under the reaction conditions. The synthetic route employed was shown to be compatible with a variety of 4-oxoazetidine-2-carbaldehydes, ol-amino esters, or dipolarophiles, offering a versatile entry to pyrrolizidine systems.
引用
收藏
页码:1351 / 1358
页数:8
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