New synthesis of fused tricyclic 2-azetidinones using stereoselective allylation of cis-4-formyl-β-lactams and intramolecular Diels-Alder reaction

被引：20
作者：
Alcaide, B [1 ]
Almendros, P [1 ]
机构：
[1] Univ Complutense Madrid, Fac Quim, Dept Quim Organ 1, E-28040 Madrid, Spain
来源：
TETRAHEDRON LETTERS | 1999年 / 40卷 / 05期
关键词：
D O I：
10.1016/S0040-4039(98)02513-1
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Tin(IV) chloride promoted addition of allyltrimethylsilane to cis-4-formyl-2-azetidinones 1 gives 4-[(1'-hydroxy)homoallyl]-beta-lactams 2 with excellent stereoselectivities. The mesylates of alcohols 2 are used for the diastereoselective preparation of both 4-butadienyl-2-azetidinones 6 and fused tricyclic beta-lactams 3 through a tandem one-pot elimination-intramolecular Diels-Alder reaction. (C) 1999 Elsevier Science Ltd. All rights reserved.
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页码：1015 / 1018
页数：4
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