Enantioselective Synthesis of 4-Hydroxy-2-cyclohexenones through a Multicomponent Cyclization

Three metal cooperation promotes the one‐pot selective coupling of a chromium carbene complex, an imide lithium enolate, and a propargylic organomagnesium reagent giving access to novel and densely functionalized 4‐allenyl‐2‐cyclohexenones (see scheme). These useful synthetic intermediates have been...

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Published inAngewandte Chemie (International ed.) Vol. 49; no. 50; pp. 9720 - 9724
Main Authors Barluenga, José, Suero, Marcos G, De la Campa, Raquel, Flórez, Josefa
Format Journal Article
LanguageEnglish
Published Weinheim Wiley-VCH Verlag 10.12.2010
WILEY-VCH Verlag
WILEY‐VCH Verlag
Wiley
Subjects
2-cyclohexenones
asymmetric synthesis
carbene ligands
carbocyclization
Chemistry
Chemistry, Multidisciplinary
multicomponent reactions
Physical Sciences
Science & Technology
multicomponent reactions
ORGANIC-SYNTHESIS
carbocyclization
ASYMMETRIC-SYNTHESIS
OPTICALLY-ACTIVE 2,3-ALLENOLS
carbene ligands
EFFICIENT SYNTHESIS
ALDOL REACTIONS
PROPARGYL
2-cyclohexenones
MICHAEL ADDITION
ALCOHOLS
FISCHER CARBENE COMPLEXES
asymmetric synthesis
CHEMISTRY
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Summary:Three metal cooperation promotes the one‐pot selective coupling of a chromium carbene complex, an imide lithium enolate, and a propargylic organomagnesium reagent giving access to novel and densely functionalized 4‐allenyl‐2‐cyclohexenones (see scheme). These useful synthetic intermediates have been prepared through a cyclization process that involves newly reported reaction steps and an unusually high level of asymmetric induction.
Bibliography:http://dx.doi.org/10.1002/anie.201004413
MEC of Spain - No. CTQ2007-61048/BQU
ark:/67375/WNG-DTZP2CG0-H
Principado de Asturias - No. IB08-088
istex:A62A9221CB0FBAA48AFCEC37E9EFCED76BC34BE6
ArticleID:ANIE201004413
Financial support of this work by the MEC of Spain (grant no. CTQ2007-61048/BQU) and the Principado de Asturias (project no. IB08-088) is gratefully acknowledged. M.G.S. and R.D.C. thank the MEC of Spain for a FPU predoctoral fellowship.
Financial support of this work by the MEC of Spain (grant no. CTQ2007‐61048/BQU) and the Principado de Asturias (project no. IB08‐088) is gratefully acknowledged. M.G.S. and R.D.C. thank the MEC of Spain for a FPU predoctoral fellowship.
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ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201004413