Organic Letters
Organic Letters
5 years ago

Enantioselective Three-Component Assembly of β′-Aryl Enones Using a Rhodium-Catalyzed Alkyne Hydroacylation/Aryl Boronic Acid Conjugate Addition Sequence

Enantioselective Three-Component Assembly of β′-Aryl Enones Using a Rhodium-Catalyzed Alkyne Hydroacylation/Aryl Boronic Acid Conjugate Addition Sequence
Michael C. Willis, Ming Gao
Rhodium-catalyzed alkyne hydroacylation using alkyl β-S-aldehydes, enantioselective rhodium-catalyzed aryl boronic acid conjugate addition, and sulfide elimination are combined in sequence to provide β′-aryl enones. The reaction sequence is efficient and delivers highly functionalized products with excellent levels of enantiocontrol. Good variation of the three reaction components is demonstrated. The sequence corresponds to the formal regio- and enantioselective monoconjugate addition of aryl boronic acids to dienones.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b01087

DOI: 10.1021/acs.orglett.7b01087

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