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

Warning

This publication doesn't include Faculty of Sports Studies. It includes Central European Institute of Technology. Official publication website can be found on muni.cz.
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.
Related projects:

You are running an old browser version. We recommend updating your browser to its latest version.

More info