通过脱羧胺化反应进行分子内环外β-氨基醇的极性翻转合成
Intramolecular Umpolung Synthesis of Exocyclic β-Amino Alcohols through Decarboxylative Amination.
作者信息
Chen Jianfeng, Tian Jiaxin, Liu Feng, Liu Yong, Zhao Guoqing, Yuan Weicheng, Zhao Baoguo
机构信息
National Engineering Research Center of Chiral Drugs, Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, 16 South Yihuan Road, Chengdu 610041, China.
The Education Ministry Key Lab of Resource Chemistry and Shanghai Key Laboratory of Rare Earth Functional Materials, Shanghai Normal University, 100 Guilin Road, Shanghai 200234, China.
出版信息
ACS Omega. 2018 Nov 1;3(11):14671-14679. doi: 10.1021/acsomega.8b02324. eCollection 2018 Nov 30.
An intramolecular aminative Umpolung cyclization strategy has been developed by using α,α-diphenylglycine () as the amination and Umpolung reagent. Aldehydes () bearing an additional carbonyl group underwent condensation with α,α-diphenylglycine to form an imine, decarboxylation to generate a delocalized 2-azaallylanion, and subsequent intramolecular Umpolung cyclization to produce a variety of exocyclic β-amino alcohols () in 60-93% yields with up to >20:1 trans/cis selectivity under mild conditions.
通过使用α,α-二苯基甘氨酸（ ）作为胺化和极性转换试剂，开发了一种分子内胺化极性转换环化策略。带有额外羰基的醛（ ）与α,α-二苯基甘氨酸发生缩合反应形成亚胺，脱羧生成离域的2-氮杂烯丙基阴离子，随后进行分子内极性转换环化，在温和条件下以60-93%的产率生成多种环外β-氨基醇（ ），反式/顺式选择性高达>20:1。
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