Acyclic Stereocontrol in the Additions of Nucleophilic Alkenes to α‐Chiral N ‐Sulfonyl Imines

Autor: Barry E Rich, Jason S. Fell, Lucas W. Souza, Anna Lo, Matthew R. Duong, James C. Fettinger, Jared T. Shaw, Marilyn M. Olmstead, Martin Bravo, Jose A Moreno, Lucas C. Moore, Kendall N. Houk
Rok vydání: 2019
Předmět:
Zdroj: Chemistry – A European Journal. 25:12214-12220
ISSN: 1521-3765
0947-6539
DOI: 10.1002/chem.201902790
Popis: 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.
Databáze: OpenAIRE
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