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

共 34 条

[1] Enantioselective Aza-Henry Reaction of Seven-Membered Cyclic Imines, Dibenzo[b,f][1,4]oxazepines, by Bifunctional Organocatalysis
Shao, You-Dong
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EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2019, 2019 (09) : 1957 - 1961
[2] Synthesis and enantioselective hydrogenation of seven-membered cyclic imines: substituted dibenzo[b,f][1,4]oxazepines
Gao, Kai
Yu, Chang-Bin
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[3] Catalytic Enantioselective Aza-Reformatsky Reaction with Cyclic Imines
De Munck, Lode
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[4] Highly enantioselective direct Mannich reaction of seven-membered cyclic imines dibenzo[b,f][1,4]oxazepines with acetone via organocatalysis
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[5] Bi(OAc)3/chiral phosphoric acid catalyzed enantioselective allylation of seven-membered cyclic imines, dibenzo[b,f][1,4]oxazepines
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[6] Catalytic Asymmetric Reactions Involving the Seven-Membered Cyclic Imine Moieties Present in Dibenzo[b,f][1,4]oxazepines
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EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2018, 2018 (02) : 140 - 146
[7] Organocatalytic Enantioselective Strecker Reaction with Seven-Membered Cyclic Imines
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[8] THE REDUCTIVE METHYLATION OF DIBENZO[B,F] [1,4]OXAZEPINES
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[9] Highly Enantioselective Synthesis of 11-Substituted 10,11-Dihydrodibenzo[b,f][1,4]thiazepines through a Proline-Catalyzed Mannich Reaction of Seven-Membered Cyclic Imines with Ketones
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[10] Microwave-Assisted Synthesis of Substituted Dibenzo[b,f][1,4]thiazepines, Dibenzo[b,f][1,4]oxazepines, Benzothiazoles, and Benzimidazoles
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