Acyclic Stereocontrol in the Additions of Nucleophilic Alkenes to α-Chiral N-Sulfonyl Imines.
Lucas C MooreAnna LoJason S FellMatthew R DuongJose A MorenoBarry E RichMartin BravoJames C FettingerLucas W SouzaMarilyn M OlmsteadKendall N HoukJared T ShawPublished in: Chemistry (Weinheim an der Bergstrasse, Germany) (2019)
Diastereoselective Lewis acid-mediated additions of nucleophilic alkenes to N-sulfonyl imines are reported. The canonical polar Felkin-Anh model describing additions to carbonyls does not adequately describe analogous additions to N-sulfonyl imines. Herein, we describe the development of conditions to produce both syn and anti products with high diastereoselectivity and good yields. A stereoelectronic model consistent with experimental outcomes is also proposed.