Synthesis of vinyl spirolactones and lactams by sequential cross-coupling metathesis, [2+2] photocycloaddition and cyclobutane ring-opening

被引：15

作者：

Faure, S

Piva-Le Blanc, S

Piva, O ^{[1
]}

机构：

[1] Univ Reims, Lab Photochim, CNRS, UMR 6519, F-51687 Reims, France

[2] Univ Lyon 1, Lab Chim Organ Photochim & Synth, CNRS, UMR 5622, F-69622 Villeurbanne, France

来源：

TETRAHEDRON LETTERS | 1999年 / 40卷 / 33期

关键词：

metathesis; allyltrimethylsilane; cyclobutane; spirolactone; spirolactam;

D O I：

10.1016/S0040-4039(99)01173-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Unsaturated oxoesters and amides have been submitted to cross-coupling metathesis with trimethylallylsilane using Grubbs' catalyst. The resulting allylsilanes underwent, under irradiation, intramolecular [2+2] photocycloaddition leading to trimethylsilylmethylcyclobutanes. By treatment with an appropriate Lewis acid, vinyl spiranic lactones and lactams were isolated in good yields. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：6001 / 6004

页数：4

共 32 条

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