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

Xuelong Qiao; Jiwei Xu; Haibing He; Shuanhu Gao

doi:10.1021/acs.orglett.4c04177

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

Xuelong Qiao
, Jiwei Xu
, Haibing He
, Shuanhu Gao^*

^*此作品的通讯作者

化学与分子工程学院

East China Normal University

科研成果: 期刊稿件 › 文章 › 同行评审

1 引用（Scopus）

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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.

源语言	英语
页（从-至）	11005-11010
页数	6
期刊	Organic Letters
卷	26
期	50
DOI	https://doi.org/10.1021/acs.orglett.4c04177
出版状态	已出版 - 20 12月 2024

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

abstract = "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{\textquoteright}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.",

author = "Xuelong Qiao and Jiwei Xu and Haibing He and Shuanhu Gao",

note = "Publisher Copyright: {\textcopyright} 2024 American Chemical Society",

year = "2024",

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doi = "10.1021/acs.orglett.4c04177",

language = "英语",

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TY - JOUR

T1 - Enantioselective Excited-State Nazarov Reaction

T2 - A Relay Strategy of Electrocyclization and Parallel Kinetic Resolution

AU - Qiao, Xuelong

AU - Xu, Jiwei

AU - He, Haibing

AU - Gao, Shuanhu

PY - 2024/12/20

Y1 - 2024/12/20

N2 - 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.

AB - 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.

UR - https://www.scopus.com/pages/publications/85211478871

U2 - 10.1021/acs.orglett.4c04177

DO - 10.1021/acs.orglett.4c04177

M3 - 文章

C2 - 39643589

AN - SCOPUS:85211478871

SN - 1523-7060

VL - 26

SP - 11005

EP - 11010

JO - Organic Letters

JF - Organic Letters

IS - 50

ER -

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

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