非循环立体控制在亲核烯烃对α-手性 N-磺酰亚胺加成反应中的应用。
Acyclic Stereocontrol in the Additions of Nucleophilic Alkenes to α-Chiral N-Sulfonyl Imines.
机构信息
Department of Chemistry and Biochemistry, University of California, One Shields Ave., Davis, CA 95616, USA.
Department of Chemistry, University of California, Los Angeles, 607 Charles E. Young Drive East, Los Angeles, CA 90095-1569, USA.
出版信息
Chemistry. 2019 Sep 18;25(52):12214-12220. doi: 10.1002/chem.201902790. Epub 2019 Aug 21.
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.
本文报道了亲核烯烃与 N-磺酰亚胺的立体选择性路易斯酸介导加成反应。描述羰基加成的经典极性 Felkin-Anh 模型不能充分描述类似的 N-磺酰亚胺加成反应。本文描述了开发条件以高产率获得高立体选择性的顺式和反式产物。还提出了一个与实验结果一致的立体电子模型。
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