Enantioselective Excited-State Nazarov Reaction: A Relay Strategy of Electrocyclization and Parallel Kinetic Resolution

被引：0
|
作者：
Qiao, Xuelong [1 ]
Xu, Jiwei [1 ]
He, Haibing [1 ]
Gao, Shuanhu [1 ,2 ]
机构：
[1] East China Normal Univ, Sch Chem & Mol Engn, Shanghai Key Lab Green Chem & Chem Proc, State Key Lab Petr Mol & Proc Engn, Shanghai 200050, Peoples R China
[2] East China Normal Univ, Wuhu Hosp, Shanghai Frontiers Sci Ctr Mol Intelligent Synth, Sch Chem & Mol Engn, Shanghai 200050, Peoples R China
来源：
ORGANIC LETTERS | 2024年 / 26卷 / 50期
基金：
中国国家自然科学基金;
关键词：
1-CYCLOHEXENYL PHENYL KETONE; CYCLIZATION; PHOTOCHEMISTRY;
D O I：
10.1021/acs.orglett.4c04177
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
We report herein the enantioselective photoinduced Nazarov reaction using a relay strategy of an electrocyclization, followed by parallel kinetic resolution (PKR). No enantioselectivity was observed during electrocyclization due to weak coordination between chiral ligands and the substrate's carbonyl group. However, PKR was successfully achieved in the deprotonation step with a bifunctional chiral thiourea ligand. Regioselective deprotonation, controlled by the chiral N,N-dimethyl amine motif, produced cis-6,5,6-fused tricyclic stereoisomers with high ee and yields.
引用
收藏
页码：11005 / 11010
页数：6
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