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

页码：1624 / 1628

页数：5

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