通过相转移催化的立体选择性分子内氮杂-Michael加成反应及手性亚磺酰胺亲核试剂实现环己二烯酮的去对称化反应
Desymmetrization of Cyclohexadienones through Phase-Transfer-Catalyzed Stereoselective Intramolecular Aza-Michael Addition with Chiral Sulfinamide Nucleophiles.
作者信息
Wu Bing-Syuan, Chao Yu-Wei, Chen Hong-Sing, Tsai Cheng-Che
机构信息
Department of Chemistry, Tunghai University, Taichung City 40704, Taiwan.
出版信息
J Org Chem. 2023 Sep 1;88(17):12835-12843. doi: 10.1021/acs.joc.3c01253. Epub 2023 Aug 10.
PMID:37562968
Abstract
This paper reports the desymmetrization of cyclohexadienones through stereoselective intramolecular aza-Michael addition with a tethered chiral sulfinamide nucleophile. The reaction was facilitated by phase-transfer catalysis and produced various nitrogen-containing bicyclic compounds with a yield of up to 93% and a diastereomeric ratio of up to >20:1.
摘要
本文报道了通过与 tethered 手性亚磺酰胺亲核试剂进行立体选择性分子内氮杂-Michael 加成实现环己二烯酮的去对称化反应。该反应通过相转移催化得以促进，生成了各种含氮双环化合物，产率高达 93%，非对映体比例高达>20:1。
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