trans-Hydroalumination/Alkylation: One-Pot Synthesis of Trisubstituted Allylic Alcohols
Described herein is a method of stereoselective synthesis of trisubstituted allylic alcohols by alkylation of alkenyl alanates, formed in situ through treatment of propargyl alcohols with Vitride (Red-Al). This technique represents the first of its kind to feature a trans-hydrometalation, and is par...
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Published in | Organic letters Vol. 8; no. 17; pp. 3761 - 3764 |
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Main Authors | , |
Format | Journal Article |
Language | English |
Published |
WASHINGTON
American Chemical Society
17.08.2006
Amer Chemical Soc |
Subjects | |
Online Access | Get full text |
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Summary: | Described herein is a method of stereoselective synthesis of trisubstituted allylic alcohols by alkylation of alkenyl alanates, formed in situ through treatment of propargyl alcohols with Vitride (Red-Al). This technique represents the first of its kind to feature a trans-hydrometalation, and is particularly effective for the formation of 1,4-dienes. Applications involving primary, secondary, and tertiary alcohols are discussed, as well as limitations regarding both alkyne and electrophile components. |
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Bibliography: | Medline NIH RePORTER ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23 |
ISSN: | 1523-7060 1523-7052 |
DOI: | 10.1021/ol0613721 |