An efficient one-pot approach to bridged bicyclic ring-systems through consecutive hetero-domino transformations: A mechanistic rationale and further rearrangements

被引：27

作者：

Finet, L ^{[1
]}

Lena, JIC ^{[1
]}

Kaoudi, T ^{[1
]}

Birlirakis, N ^{[1
]}

Arseniyadis, S ^{[1
]}

机构：

[1] CNRS, Inst Chim Subst Nat, F-91198 Gif Sur Yvette, France

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2003年 / 9卷 / 16期

关键词：

Baeyer-Villiger oxidation; configuration inversion; domino reactions; ring expansion; ring-system interchange;

D O I：

10.1002/chem.200304838

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

This article describes the design of olefin-generated/reagent-modulated consecutive hetero-domino reactions of 1,2-unsaturated bicyclic diols, which are potentially of great use, initiated by PhI(OAc)(2), continued by [Pb(OAc)(4)], and completed by use of a mild base (K2CO3). Inversion of a quaternary center has been achieved through a three-reaction sequence: a domino transformation followed by an m-CPBA-mediated Baeyer-Villiger oxidation and subsequent reductive lactone ring opening.

引用

页码：3813 / 3820

页数：8

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