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

David M. Aparicio; Joel L. Terán; Luis F. Roa; Dino Gnecco; Jorge R. Juárez; María L. Orea; Angel Mendoza; Marcos Flores-Alamo; Laurent Micouin

doi:10.1055/s-0030-1260064

PAPER

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

David M. Aparicio^a, Joel L. Terán*^a, Luis F. Roa^b, Dino Gnecco^a, Jorge R. Juárez^a, María L. Orea^a, Angel Mendoza^a, Marcos Flores-Alamo^c, Laurent Micouin^d
^a Centro de Química, Benemérita Universidad Autónoma de Puebla, Edif. 103F Complejo de Ciencias, C.U., 72570 Puebla, Pue., México
Fax: +52(222)229551; e-Mail: joelluisteran@hotmail.com;
^b División Académica de Ciencias Básicas, Universidad Juárez Autónoma de Tabasco, 86690 Cunduacán, Tab., México
^c Facultad de Química, Universidad Nacional Autónoma de México, 04510 México, DF, México
^d Laboratoire de Chimie Thérapeutique, UMR 8638 associée au CNRS et à l’Université Paris Descartes, Faculté des Sciences Pharmaceutiques et Biologiques, 4 av de l’Observatoire, 75270 Paris cedex 06, France

Abstract

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Abstract

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.

Key words

chemoselectivity - cyclization - alkoxide - oxazepan-5-ones - morpholin-3-ones

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References

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