C−C Bond Formation between Fischer Carbene Complexes and Allylic Alcohols by a [3,4] Sigmatropic Rearrangement Promoted by a [1,2] M(CO)5 Shift

A [1,2] M(CO)5 shift promotes a [3,4] sigmatropic rearrangement after the addition of allylic alcohols to Fischer alkenylcarbene complexes of tungsten or chromium in the presence of alkoxide ions. This opens a new synthetic route to the adducts 1. The reaction is also applicable to propargylic alcoh...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 1999-04, Vol.38 (8), p.1091-1093
Main Authors: Barluenga, José, Rubio, Eduardo, López-Pelegrín, José A., Tomás, Miguel
Format: Article
Language:English
Subjects:
Carbene complexes
Chromium
Orthoesters
Rearrangements
Tungsten
Online Access:Get full text
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Summary:A [1,2] M(CO)5 shift promotes a [3,4] sigmatropic rearrangement after the addition of allylic alcohols to Fischer alkenylcarbene complexes of tungsten or chromium in the presence of alkoxide ions. This opens a new synthetic route to the adducts 1. The reaction is also applicable to propargylic alcohols. [M]=Mo(CO)5, W(CO)5.
ISSN:1433-7851
1521-3773
DOI:10.1002/(SICI)1521-3773(19990419)38:8<1091::AID-ANIE1091>3.0.CO;2-5