Acyclic Stereocontrol in the Additions of Nucleophilic Alkenes to α‐Chiral N ‐Sulfonyl Imines
Acyclic Stereocontrol in the Additions of Nucleophilic Alkenes to α‐Chiral N ‐Sulfonyl Imines
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亲核烯烃与手性 N 磺酰亚胺加成的非环立体控制
DOI：
10.1002/chem.201902790
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发表时间：
2019
期刊：
影响因子：
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通讯作者：
Olmstead, Marilyn M.
中科院分区：
文献类型：
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作者：
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.
据报道，非对映选择性路易斯酸介导的亲核烯烃与 N-磺酰亚胺的加成反应。描述羰基加成的规范极性 Felkin-Anh 模型并不能充分描述 N-磺酰亚胺的类似加成。在此，我们描述了生产具有高非对映选择性和良好产率的同义产物和反产物的条件的开发。还提出了与实验结果一致的立体电子模型。
Diastereoselective Lewis acid‐mediated additions of nucleophilic alkenes toN‐sulfonyl imines are reported. The canonical polar Felkin–Anh model describing additions to carbonyls does not adequately describe analogous additions toN‐sulfonyl imines. Herein, we describe the development of conditions to produce bothsynandantiproducts with high diastereoselectivity and good yields. A stereoelectronic model consistent with experimental outcomes is also proposed.