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Asymmetric One‐Pot Conjugate Addition of Grignard Reagents to α,β‐Unsaturated Compounds Followed by Reaction with Carbenium Ions
Author(s) -
Drusan Michal,
Rakovský Erik,
Marek Jaromír,
Šebesta Radovan
Publication year - 2015
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201500074
Subject(s) - chemistry , enantioselective synthesis , conjugate , diastereomer , reagent , catalysis , ion , organic chemistry , addition reaction , combinatorial chemistry , medicinal chemistry , mathematical analysis , mathematics
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.