Citation: Xue Zai-Kun, Fu Nian-Kai, Luo San-Zhong. Asymmetric hydroazidation of α-substituted vinyl ketones catalyzed by chiral primary amine[J]. Chinese Chemical Letters, ;2017, 28(5): 1083-1086. doi: 10.1016/j.cclet.2017.01.014 shu

Asymmetric hydroazidation of α-substituted vinyl ketones catalyzed by chiral primary amine

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

Corresponding author: Luo San-Zhong, luosz@iccas.ac.cn
Received Date: 12 November 2016
Revised Date: 30 December 2016
Accepted Date: 16 January 2017
Available Online: 22 May 2017

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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.
- Chiral primary amine catalysis,
- Hydroazidation,
- Enamine protonation,
- α-Substituted vinyl ketones,
- Aza-Michael addition,
- Chiral β-azido ketones
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