Acyclic Stereocontrol in the Additions of Nucleophilic Alkenes to α‐Chiral N‐Sulfonyl Imines. Issue 52 (21st August 2019)

• Record Type: Journal Article
• Authors: Moore, Lucas C.; Lo, Anna; Fell, Jason S.; Duong, Matthew R.; Moreno, Jose A.; Rich, Barry E.; Bravo, Martin; Fettinger, James C.; Souza, Lucas W.; Olmstead, Marilyn M.; Houk, Kendall N.; Shaw, Jared T.
• Is Part Of: Chemistry. Volume 25:Issue 52(2019)
• Page Start: 12214
• Page End: 12220
• Publication Date: 2019-08-21
• Subjects: ab initio calculations -- allylation -- diastereoselectivity -- Lewis acids -- N-sulfonyl imines; Chemistry -- Periodicals; 540
• DOI: 10.1002/chem.201902790
• Languages: English
• ISSNs: 0947-6539

Abstract

Abstract: 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. Abstract : Dealing with models : A synthetic method for the addition of nucleophilic alkenes to access α‐chiral N ‐sulfonyl imines with acyclic stereocontrol is presented. Optimal conditions have been developed to produce both syn and anti isomers with high diastereoselectivity and good yields. Additionally, a stereoelectronic model consistent with the outcome of these transformations is also proposed.