Issue 91, 2015

Highly enantioselective direct allylic alkylation of butenolides with Morita–Baylis–Hillman carbonates catalyzed by chiral squaramide-phosphine

Abstract

An efficient asymmetric vinylogous allylic alkylation of β,γ-butenolides with Morita–Baylis–Hillman carbonates has been developed. With a chiral cyclohexane-based squaramide-phosphine catalyst 5e, optically active γ,γ-disubstituted butenolides containing adjacent quaternary and tertiary chiral centers have been constructed in good-to-excellent yields (up to 98%) and excellent stereoselectivities (87 : 13–99 : 1 dr, 96–99% ee).

Graphical abstract: Highly enantioselective direct allylic alkylation of butenolides with Morita–Baylis–Hillman carbonates catalyzed by chiral squaramide-phosphine

Supplementary files

Article information

Article type
Communication
Submitted
24 Jul 2015
Accepted
21 Aug 2015
First published
24 Aug 2015

RSC Adv., 2015,5, 74170-74173

Highly enantioselective direct allylic alkylation of butenolides with Morita–Baylis–Hillman carbonates catalyzed by chiral squaramide-phosphine

T. Kang, X. Zhao, F. Sha and X. Wu, RSC Adv., 2015, 5, 74170 DOI: 10.1039/C5RA14667D

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