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Highly Enantioselective Insertion of Carbenoids into N[BOND]H Bonds Catalyzed by Copper(I) Complexes of Binol Derivatives

Authors

  • Zongrui Hou,

    1. Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry, Sichuan University Chengdu 610064 (China), Fax: (+86) 28-8541-8249
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  • Jun Wang Dr.,

    1. Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry, Sichuan University Chengdu 610064 (China), Fax: (+86) 28-8541-8249
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  • Peng He,

    1. Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry, Sichuan University Chengdu 610064 (China), Fax: (+86) 28-8541-8249
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  • Jing Wang,

    1. Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry, Sichuan University Chengdu 610064 (China), Fax: (+86) 28-8541-8249
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  • Bo Qin Dr.,

    1. Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry, Sichuan University Chengdu 610064 (China), Fax: (+86) 28-8541-8249
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  • Xiaohua Liu Dr.,

    1. Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry, Sichuan University Chengdu 610064 (China), Fax: (+86) 28-8541-8249
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  • Lili Lin Dr.,

    1. Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry, Sichuan University Chengdu 610064 (China), Fax: (+86) 28-8541-8249
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  • Xiaoming Feng Prof. Dr.

    1. Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry, Sichuan University Chengdu 610064 (China), Fax: (+86) 28-8541-8249
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  • We acknowledge the National Natural Science Foundation of China (Nos. 20702033 and 20732003), the PCSIRT (No. IRT0846), and the National Basic Research Program of China (973 Program) (No. 2010CB833300) for financial support. We also thank the Sichuan University Analytical & Testing Center for NMR analysis and the State Key Laboratory of Biotherapy for HRMS analysis.

Abstract

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Secondary amines do it too! Catalytic asymmetric insertion of α-diazoesters in the N[BOND]H bond of differently substituted amines has been successfully achieved (see scheme; M.S.=molecular sieves). For a wide substrate scope, excellent enantioselectivities (up to 98 % ee) and high yields (up to 99 %) were obtained under mild reaction conditions.

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