Stereoisomerically Pure Trisubstituted Vinylaluminum Reagents and their Utility in Copper-Catalyzed Enantioselective Synthesis of 1,4-Dienes Containing Z or E Alkenes

The desired isomer of a chiral 1,4‐diene containing an E or Z double bond can be accessed readily by a regio‐ and stereoselective hydroalumination of silyl‐substituted alkynes and subsequent enantioselective copper‐catalyzed allylic alkylation. The utility of the procedure was demonstrated through t...

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Bibliographic Details
Published inAngewandte Chemie (International ed.) Vol. 49; no. 2; pp. 419 - 423
Main Authors Akiyama, Katsuhiro, Gao, Fang, Hoveyda, Amir H
Format Journal Article
LanguageEnglish
Published Weinheim Wiley-VCH Verlag 01.01.2010
WILEY-VCH Verlag
WILEY‐VCH Verlag
Wiley
Subjects
Alkenes - chemical synthesis
Alkylation
allylic alkylation
Aluminum Compounds - chemistry
Catalysis
Chemistry
Chemistry, Multidisciplinary
Copper - chemistry
enantioselective catalysis
hydroalumination
Indicators and Reagents
Magnetic Resonance Spectroscopy
N-heterocyclic carbenes
Physical Sciences
Science & Technology
Stereoisomerism
Vinyl Compounds - analysis
vinylaluminum reagents
ORGANOMETALLIC COMPOUNDS
ASYMMETRIC 1,4-ADDITION
VINYLATION
HYDROSILYLATION
hydroalumination
ALKYNES
vinylaluminum reagents
allylic alkylation
HYDRALUMINATION
ADDITIONS
enantioselective catalysis
METATHESIS
N-heterocyclic carbenes
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Summary:The desired isomer of a chiral 1,4‐diene containing an E or Z double bond can be accessed readily by a regio‐ and stereoselective hydroalumination of silyl‐substituted alkynes and subsequent enantioselective copper‐catalyzed allylic alkylation. The utility of the procedure was demonstrated through the synthesis of (−)‐nyasol (see scheme). dibal‐H=diisobutylaluminum hydride, NHC=N‐heterocyclic carbene.
Bibliography:http://dx.doi.org/10.1002/anie.200905223
istex:68C24D49674D5B2133C9DFE2D5BEC7D1DDDE7FDD
ark:/67375/WNG-BGN6JB0V-D
The NIH (Grant GM-47480) provided financial support. Mass spectrometry facilities at Boston College are supported by the NSF (CHE-0619576).
NIH - No. GM-47480
ArticleID:ANIE200905223
NSF - No. CHE-0619576
The NIH (Grant GM‐47480) provided financial support. Mass spectrometry facilities at Boston College are supported by the NSF (CHE‐0619576).
NIH RePORTER
ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.200905223