Chemodivergence in alkene/allene cycloetherification of enallenols: Iron versus noble metal catalysis

被引：38

作者：

Alcaide, Benito ^{[1
]}

Almendros, Pedro ^{[2
]}

Martinez del Campo, Teresa ^{[1
]}

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：

CHEMISTRY-A EUROPEAN JOURNAL | 2008年 / 14卷 / 26期

关键词：

alkenes; allenes; chemoselectivity; heterocycles; iron;

D O I：

10.1002/chem.200801166

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A method was proposed for chemo-differentiation between an alkene and an allene moiety using iron- or precious-metal catalysis. Chemodivergence in alkene and allene were also reported by cycloetherification of enallenols. It was observed that racemic enallenols were prepared from the 4-oxoazetidine-2- carbaldehyde through regio-controlled indium-mediated Barbier carbonyl-allenylation reactions. Prenylation and allenylation process were used to prepare an optically active non-β-lactam precursors from (R)-2,3-O-isopropylideneglyceraldehyde. The effects of different metal catalysis in the chemoselectivity of the hydroalkoxylation reaction were also observed during the study. The Lewis-acid catalyzed cyclization of unsaturated alcohol was examined in the presence of different metallic chlorides.

引用

页码：7756 / 7759

页数：4

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