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.
Related projects:	CEITEC - open access