Catalytic enantioselective aza-Reformatsky reaction with seven-membered cyclic imines dibenzo[b,f][1,4]oxazepines

被引：20
|
作者：
De Munck, Lode [1 ]
Sukowski, Verena [1 ]
Vila, Carlos [1 ]
Carmen Munoz, M. [2 ]
Pedro, Jose R. [1 ]
机构：
[1] Univ Valencia, Fac Quim, Dept Quim Organ, Dr Moliner 50, E-46100 Valencia, Spain
[2] Univ Politecn Valencia, Dept Fis Aplicada, Camino Vera S-N, E-46022 Valencia, Spain
来源：
ORGANIC CHEMISTRY FRONTIERS | 2017年 / 4卷 / 08期
关键词：
BETA-AMINO ACIDS; POTENT PGE(2) ANTAGONIST; PHARMACOLOGICAL EVALUATION; ASYMMETRIC HYDROGENATION; REVERSE-TRANSCRIPTASE; CHEMISTRY; DERIVATIVES; KETONES; DIACYLHYDRAZINE; (&)-MELITENSIN;
D O I：
10.1039/c7qo00329c
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A catalytic enantioselective aza-Reformatsky reaction is reported with cyclic dibenzo[b,f][1,4]oxazepines and ethyl iodoacetate leading to the synthesis of chiral ethyl 2-(10,11-dihydrodibenzo[b,f][1,4]oxazepin-11- yl)acetate derivatives with excellent yields and high enantioselectivities (up to 98% yield and 97 : 3 er) using a readily available diaryl prolinol L4 as the chiral ligand and Me2Zn as the zinc source under an air atmosphere. Furthermore, different transformations were carried out with the corresponding chiral beta-amino esters, preserving in all cases the optical purity.
引用
收藏
页码：1624 / 1628
页数：5
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