Asymmetric One-Pot Conjugate Addition of Grignard Reagents to alpha,beta-Unsaturated Compounds Followed by Reaction with Carbenium Ions

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Authors

DRUSAN Michal RAKOVSKÝ Erik MAREK Jaromír ŠEBESTA Radovan

Year of publication 2015
Type Article in Periodical
Magazine / Source ADVANCED SYNTHESIS & CATALYSIS
MU Faculty or unit

Central European Institute of Technology

Citation
Web http://onlinelibrary.wiley.com/doi/10.1002/adsc.201500074/abstract;jsessionid=6039F4AD8F14C5AFBD11F8B684CAF703.f03t04
Doi http://dx.doi.org/10.1002/adsc.201500074
Field Organic chemistry
Keywords asymmetric catalysis; carbocations; conjugate addition; domino reactions; ferrocene ligands
Description Asymmetric catalytic multistep reactions enable the formation of structurally complex compounds from simple starting materials. Enantioselective Cu-catalyzed 1,4-additions of Grignard reagents to Michael acceptors form reactive chiral enolates. We show here that these chiral enolates react in a one-pot fashion with naked carbenium ions, such as tropylium, 1,3-benzodithiolium, and dianisylmethylium ions. The corresponding products were obtained in good yields, with enantioselectivities up to 96% ee and high diastereomeric purities.
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