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
收藏
页码：2310 / 2320
页数：11
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