Enantioselective Stetter Reactions Catalyzed by Bis(amino)cyclopropenylidenes: Important Role for Water as an Additive
Date
2020-12-15Author
Rezazadeh Khalkhali, Mehran
Wilde, Myron M. D.
Gravel, Michel
Publisher
ACS PublicationsType
ArticlePeer Reviewed Status
Peer ReviewedMetadata
Show full item recordAbstract
The first highly enantioselective intermolecular Stetter reaction using simple enones is reported. A series of novel chiral BAC structures were designed and prepared. They were tested in the Stetter reaction with simple aldehydes and enones. The products were generated in excellent yields and enantioselectivities (up to 92% ee). Surprisingly, a substoichiometric amount of water was crucial to obtain high enantioselectivities. Chiral BACs were also shown to catalyze 1,6-conjugate addition reactions with paraquinone methides enantioselectively.