ANIPE-Ligand-Enabled Copper-Catalyzed Asymmetric Carboboronation of Allenes with Imines and Diborons

doi:10.6023/cjoc202401027

Chinese Journal of Organic Chemistry Previous Articles Next Articles

ARTICLE

ANIPE配体促进的铜催化联烯与亚胺和联硼试剂的不对称碳硼化反应

刘晓东, 施世良^*

中国科学院上海有机化学研究所金属有机化学国家重点实验室上海 200032

收稿日期:2024-01-20 修回日期:2024-03-04

ANIPE-Ligand-Enabled Copper-Catalyzed Asymmetric Carboboronation of Allenes with Imines and Diborons

Xiao-Dong Liu, Shi-Liang Shi^*

State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032

Received:2024-01-20 Revised:2024-03-04
Contact: * E-mail: shiliangshi@sioc.ac.cn
Supported by:
National Key R&D Program of China (2022YFA1503702, 2021YFF0701600), the National Natural Science Foundation of China (22325110, 92256303, 21821002, 22171280), the Strategic Priority Research Program of the Chinese Academy of Sciences (XDB0610000), the Program of Shanghai Academic Research Leader (22XD1424900), the CAS Youth Interdisciplinary Team (JCTD-2021-11) and the Ningbo Natural Science Foundation (2022J017).

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Abstract

A diastereo- and enantioselective copper-catalyzed carboboronation of allene with aldimines and diborons under mild conditions is developed. This protocol is enabled by a chiral ANIPE-based copper catalyst, providing a facile and efficient approach to chiral homoallylic amines bearing two adjacent stereocenters with high enantioselectivities and diastereoselectivities. Besides, aldiminoester and ketiminoester could both serve as competent electrophiles for the production of enantioenriched α-amino esters.

Key words: NHC ligand, Copper catalysis, Chiral amine, Carboboronation

Cite this article

Xiao-Dong Liu, Shi-Liang Shi. ANIPE-Ligand-Enabled Copper-Catalyzed Asymmetric Carboboronation of Allenes with Imines and Diborons[J]. Chinese Journal of Organic Chemistry, doi: 10.6023/cjoc202401027.

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ANIPE配体促进的铜催化联烯与亚胺和联硼试剂的不对称碳硼化反应

ANIPE-Ligand-Enabled Copper-Catalyzed Asymmetric Carboboronation of Allenes with Imines and Diborons

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