Stereoselective synthesis of 1,2,3-trisubstituted 1,3-dienes through novel [3,3]-sigmatropic rearrangements in α-allenic methanesulfonates:: Application to the preparation of fused tricyclic systems by tandem rearrangement/Diels-Alder reaction

被引：33

作者：

Alcaide, B ^{[1
]}

Almendros, P

Aragoncillo, C

Redondo, MC

机构：

[1] Univ Complutense Madrid, Fac Quim, Dept Quim Organ 1, E-28040 Madrid, Spain

[2] CSIC, Inst Quim Organ Gen, E-28006 Madrid, Spain

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2005年 / 2005卷 / 01期

关键词：

allenes; cycloaddition; dienes; domino reactions; sigmatropic rearrangement;

D O I：

10.1002/ejoc.200400527

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An unprecedented stereoselective and general synthesis of 1,2,3-trisubstituted 1,3-dienes' from alpha-allenols just by treatment with a methanesulfonyl chloride/tertiary amine system has been developed. This transformation might be tentatively explained in terms of a migration of the methanesulfonyl group in the initially formed alpha-allenic methanesulfonate to give the corresponding mesyloxy-diene through a [3,3]-sigmatropic rearrangement. This reactivity pattern was incorporated into a domino process, allowing the development of a novel one-pot synthetic strategy for the preparation of fused tricycles from monocyclic allenols, masked functionalized dienes, when subjected to a domino allenol transposition/intramolecular Diels-Alder reaction process. (C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005.

引用

页码：98 / 106

页数：9

共 52 条

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