Synthesis of Chiral Endocyclic Allenes and Alkynes via Pd-Catalyzed Asymmetric Higher-Order Dipolar Cycloaddition

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期刊论文

作者：

Shi, Bin;Xiao, Meng;Zhao, Jin-Pu;Zhang, Zhihan*;Xiao, Wen-Jing;...

通讯作者：

Zhang, Zhihan;Lu, LQ

作者机构：

[Lu, Liang-Qiu; Lu, LQ; Zhang, Zhihan; Xiao, Meng; Xiao, Wen-Jing; Zhao, Jin-Pu; Shi, Bin] Cent China Normal Univ, Coll Chem, Engn Res Ctr Photoenergy Utilizat Pollut Control &, Minist Educ, Wuhan 430079, Peoples R China.

[Xiao, Wen-Jing] Wuhan Inst Photochem & Technol, Wuhan 430082, Hubei, Peoples R China.

[Lu, Liang-Qiu; Lu, LQ] Henan Normal Univ, Sch Chem & Chem Engn, Xinxiang 453007, Peoples R China.

[Lu, Liang-Qiu; Lu, LQ] Chinese Acad Sci, Lanzhou Inst Chem Phys LICP, State Key Lab Oxo Synth & Select Oxidat, Lanzhou 730000, Peoples R China.

通讯机构：

[Lu, LQ ; Zhang, ZH] C

Cent China Normal Univ, Coll Chem, Engn Res Ctr Photoenergy Utilizat Pollut Control &, Minist Educ, Wuhan 430079, Peoples R China.

Henan Normal Univ, Sch Chem & Chem Engn, Xinxiang 453007, Peoples R China.

Chinese Acad Sci, Lanzhou Inst Chem Phys LICP, State Key Lab Oxo Synth & Select Oxidat, Lanzhou 730000, Peoples R China.

语种：

英文

期刊：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

ISSN：

0002-7863

年：

2024

卷：

146

期：

页码：

26622-26629

DOI：

10.1021/jacs.4c10328

基金类别：

National Key R&D Program of China [2023YFA1507203]; National Natural Science Foundation of China [22271113, 22471089, 92256301, 22203034]; Central China Normal University; Wuhan Institute of Photochemistry and Technology

机构署名：

本校为第一机构

院系归属：

化学学院

摘要：

A Pd-catalyzed asymmetric higher-order dipolar cycloaddition between allenyl carbonates and azadienes is achieved by exploiting novel alkylidene-π-allyl-Pd dipoles. This research provides a modular platform for the synthesis of challenging chiral endocyclic allenes bearing a medium-sized heterocyclic motif and a centrally chiral stereocenter in good yields with high enantio- and diastereoselectivities (29 examples, up to 97% yield, 97:3 er and >19:1 dr). Experimental and computational studies elucidate the possible reaction mechanism and the o...

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Synthesis of Chiral Endocyclic Allenes and Alkynes via Pd-Catalyzed Asymmetric Higher-Order Dipolar Cycloaddition

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