通过NHC催化的环己二烯酮连接烯醛的高对映选择性高烯醇化物迈克尔加成/酯化序列
A Highly Enantioselective Homoenolate Michael Addition/Esterification Sequence of Cyclohexadienone-Tethered Enals via NHC Catalysis.
作者信息
Wang Ya-Jie, Wang Yi-Fan, Kang Wen-Yu, Lu Wen-Ya, Wang Yu-Hui, Tian Ping
机构信息
The Research Center of Chiral Drugs, Shanghai Frontiers Science Center for TCM Chemical Biology, Innovation Research Institute of Traditional Chinese Medicine, Shanghai University of Traditional Chinese Medicine, 1200 Cailun Road, Shanghai 201203, China.
出版信息
Org Lett. 2023 Feb 3;25(4):630-635. doi: 10.1021/acs.orglett.2c04183. Epub 2023 Jan 20.
Reported here is a highly enantioselective homoenolate Michael addition/esterification sequence of cyclohexadienone-tethered enals via N-heterocyclic carbene (NHC) catalysis, affording the enantiopure -hydrobenzofurans, -hydroindoles, and -hydroindenes. The NHC catalyst bearing a nitro group greatly enhances the stereocontrol, and a bulky -aryl substituent of the triazolium salt in the catalyst is helpful for inhibiting the further aldol condensation after homoenolate Michael addition. The utility of this protocol is highlighted by a gram-scale experiment and versatile downstream transformations.
本文报道了一种通过N-杂环卡宾（NHC）催化的环己二烯酮连接烯醛的高度对映选择性同烯醇化物迈克尔加成/酯化序列，得到对映体纯的β-氢苯并呋喃、β-氢吲哚和β-氢茚。带有硝基的NHC催化剂极大地增强了立体控制，催化剂中三唑鎓盐的大位阻β-芳基取代基有助于抑制同烯醇化物迈克尔加成后的进一步羟醛缩合。克级实验和多样的下游转化突出了该方法的实用性。
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