Enantioselective cycloadditions with alpha,beta-disubstituted acrylimides.
[reaction: see text] The use of N-H imide templates provides a solution to the problem of rotamer control in Lewis acid catalyzed reactions of alpha,beta-disubstituted acryloyl imides. Reactions proceed through the s-cis rotamer and with improved reactivity because A(1,3) strain is avoided. Enantioselective nitrone, nitrile oxide, and Diels-Alder cycloadditions demonstrate the principle.
Sibi
Mukund P
MP
Department of Chemistry, North Dakota State University, Fargo, North Dakota 58105-5516, USA. mukund.sibi@ndsu.edu
Ma
Zhihua
Z
Itoh
Kennosuke
K
Narayanasamy
Prabagaran
P
Jasperse
Craig P
CP