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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Bibliographic Details
Published inOrganic letters Vol. 8; no. 17; pp. 3761 - 3764
Main Authors Langille, Neil F, Jamison, Timothy F
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 17.08.2006
Amer Chemical Soc
Subjects
Alanine - analogs & derivatives
Alanine - chemistry
Alkenes - chemical synthesis
Alkenes - chemistry
Alkylation
Alkynes - chemical synthesis
Alkynes - chemistry
Aluminum - chemistry
Chemistry
Chemistry, Organic
Combinatorial Chemistry Techniques
Molecular Structure
Physical Sciences
Propanols - chemical synthesis
Propanols - chemistry
Science & Technology
Stereoisomerism
COMPLEX
REDUCTIVE ALKYLATION
STEREOCHEMISTRY
REGIOCHEMISTRY
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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.
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