Chemodivergent Synthesis of 7-Aryl/alkyl-6-hydroxy-1,4-oxazepan-5-ones and 2-[Aryl/alkyl(hydroxy)methyl]morpholin-3-ones from a Common Epoxyamide Precursor

被引：11

作者：

Aparicio, David M. ^{[1
]}

Teran, Joel L. ^{[1
]}

Roa, Luis F. ^{[2
]}

Gnecco, Dino ^{[1
]}

Juarez, Jorge R. ^{[1
]}

Orea, Maria L. ^{[1
]}

Mendoza, Angel ^{[1
]}

Flores-Alamo, Marcos ^{[3
]}

Micouin, Laurent ^{[4
,5
]}

机构：

[1] Benemerita Univ Autonoma Puebla, Ctr Quim, Puebla 72570, Pue, Mexico

[2] Univ Juarez Autonoma Tabasco, Div Acad Ciencias Basicas, Cunduacan 86690, Tab, Mexico

[3] Univ Nacl Autonoma Mexico, Fac Quim, Mexico City 04510, DF, Mexico

[4] CNRS, UMR Associee 8638, Chim Therapeut Lab, F-75270 Paris 06, France

[5] Univ Paris 05, Fac Sci Pharmaceut & Biol, F-75270 Paris 06, France

来源：

SYNTHESIS-STUTTGART | 2011年 / 14期

关键词：

chemoselectivity; cyclization; alkoxide; oxazepan-5-ones; morpholin-3-ones; HIGHLY STEREOSELECTIVE-SYNTHESIS; ASYMMETRIC-SYNTHESIS; MONOSACCHARIDE DERIVATIVES; ENANTIOSELECTIVE SYNTHESIS; NUCLEOPHILIC OPENINGS; 2,3-EPOXY ALCOHOLS; CHIRAL AUXILIARY; GLYCIDIC AMIDES; EPOXIDES; EPOXIDATION;

D O I：

10.1055/s-0030-1260064

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We present here a regiospecific synthesis of 7-alkyl- or 7-aryl-6-hydroxy-1,4-oxazepan-5-ones and 2-[aryl(hydroxy) methyl]- or 2-(1-hydroxyalkyl)morpholin-3-ones from a diastereomeric mixture of trans-3-alkyl- or -3-aryl-N-(2-hydroxyethyl)-N-(1-phenylethyl) oxirane-2-carboxamides. This chemodivergent synthesis is easily controlled by an appropriate choice of cyclization reaction conditions.

引用

页码：2310 / 2320

页数：11

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