A highly enantioselective one-pot synthesis of homoallylic alcohols via tandem asymmetric allyl transfer/olefin cross metathesis

A highly enantioselective one-pot synthesis of linear homoallylic alcohols with terminal ester functionality has been achieved. The reactions were controlled by ordered addition of reagents and catalysts, ensuring complete consumption of aldehyde. The synthetic utility of this strategy has been demo...

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Bibliographic Details
Published inTetrahedron letters Vol. 47; no. 5; pp. 809 - 812
Main Authors Lee, Cheng-Hsia Angeline, Loh, Teck-Peng
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 01.01.2006
Elsevier
Subjects
Allyl transfer
Chemistry
Chemistry, Organic
Homoallylic alcohols
Olefin cross metathesis
Physical Sciences
Science & Technology
Tandem reactions
Homoallylic alcohols
Olefin cross metathesis
Allyl transfer
Tandem reactions
olefin cross metathesis
ALPHA-ADDUCTS
OLEFIN METATHESIS
COMPONENT
allyl transfer
homoallylic alcohols
tandem reactions
CATALYSTS
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Summary:A highly enantioselective one-pot synthesis of linear homoallylic alcohols with terminal ester functionality has been achieved. The reactions were controlled by ordered addition of reagents and catalysts, ensuring complete consumption of aldehyde. The synthetic utility of this strategy has been demonstrated in a short synthesis of a low boiling point intermediate for grahamimycin A. A highly enantioselective one-pot synthesis of linear homoallylic alcohols with terminal ester functionality has been achieved. The reactions were controlled by ordered addition of reagents and catalysts, ensuring complete consumption of aldehyde. The synthetic utility of this strategy has been demonstrated in a short synthesis of a low boiling point intermediate for grahamimycin A.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2005.11.078