| Asymmetric hydroazidation of α-substituted vinyl ketones catalyzed by chiral primary amine |
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| 作者姓名： | Zai-Kun Xue Nian-Kai Fu San-Zhong Luo |
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| 作者单位： | Beijing National Laboratory for Molecular Sciences(BNLMS), CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, China |
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| 基金项目： | We thank National Natural Science Foundation of China (NSFC Nos. 21390400, 21521002 and 21502198) and the Ministry of Science and Technology, Chinese Academy of Sciences (No. QYZDJSSW-SLH023) for generous financial support. S. L. is supported by National Program for Support of Top-notch Young Professionals, CAS Youth Innovation Promotion Association and CAS onehundred talented program (D). |
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| 摘 要： | We report herein the first example of asymmetric hydroazidation of α-substituted vinyl ketones by using chiral primary amines as the catalysts.A simple chiral primary-tertiary diamine catalyst derived from lphenylalanine was found to readily promote this aza-Michael addition reaction with enamine protonation as the key stereogenic step,thus enabling the effective synthesis of α-chiral β-azido ketones with good yields and moderate enantioselectivities.
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| 关 键 词： | Chiral primary amine catalysis Hydroazidation Enamine protonation &alpha -Substituted vinyl ketones Aza-Michael addition Chiral &beta -azido ketones |
Asymmetric hydroazidation of α-substituted vinyl ketones catalyzed by chiral primary amine |
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| Zai-Kun Xue,Nian-Kai Fu,San-Zhong Luo.Asymmetric hydroazidation of α-substituted vinyl ketones catalyzed by chiral primary amine[J].Chinese Chemical Letters,2017,28(5):1083-1086. |
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| Authors: | Zai-Kun Xue Nian-Kai Fu San-Zhong Luo |
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| Institution: | Beijing National Laboratory for Molecular Sciences(BNLMS), CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, China |
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| Abstract: | We report herein the first example of asymmetric hydroazidation of α-substituted vinyl ketones by using chiral primary amines as the catalysts. A simple chiral primary-tertiary diamine catalyst derived from L-phenylalanine was found to readily promote this aza-Michael addition reaction with enamine protonation as the key stereogenic step, thus enabling the effective synthesis of α-chiral β-azido ketones with good yields and moderate enantioselectivities. |
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| Keywords: | Chiral primary amine catalysis Hydroazidation Enamine protonation α-Substituted vinyl ketones Aza-Michael addition Chiral β-azido ketones |
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