Lewis acid-mediated nucleophilic additions to α-alkoxy N-sulfonyl imines result in unexpected diastereoselectivity. As canonical polar Felkin-Anh and Cram models describing additions to α-chiral carbonyls do not adequately characterize additions to analogous N-sulfonyl imines, we describe newly optimized conditions to achieve high syn and anti selectivity in systems of this type. A novel stereoelectronic model developed with theoretical chemistry and consistent with experimental outcomes is also reported.

Acyclic stereocontrol in the additions of nucleophilic alkenes to α-chiral N-sulfonyl imines

2019 Fall National Meeting

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