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 |
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Rok vydání: | 2019 |
Předmět: |
Sulfonyl
chemistry.chemical_classification Reaction mechanism 010405 organic chemistry Chemistry Organic Chemistry General Chemistry 010402 general chemistry 01 natural sciences Catalysis 0104 chemical sciences Nucleophile Computational chemistry Ab initio quantum chemistry methods Lewis acids and bases |
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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