异恶唑烷-5-酮的有机催化多组分合成

Organocatalyzed Multicomponent Synthesis of Isoxazolidin-5-ones.

作者信息

Berini Christophe, Sebban Muriel, Oulyadi Hassan, Sanselme Morgane, Levacher Vincent, Brière Jean-François

机构信息

Normandie Univ, COBRA, UMR 6014 et FR 3038; Univ Rouen; INSA Rouen; CNRS, IRCOF , 1 rue Tesnière, 76821 Mont Saint Aignan Cedex, France.

Normandie Univ, Laboratoire SMS- EA3233, Univ Rouen , F-76821, Mont Saint Aignan, France.

出版信息

Org Lett. 2015 Nov 6;17(21):5408-11. doi: 10.1021/acs.orglett.5b02755. Epub 2015 Oct 21.

DOI:10.1021/acs.orglett.5b02755

PMID:26488447

Abstract

An unprecedented multicomponent organocatalyzed Knoevenagel-aza-Michael-cyclocondensation reaction between Meldrum's acid, hydroxylamines, and aldehydes afforded a straightforward entry to a large array of racemic and syn-diastereoenriched isoxazolidinones as synthetically useful scaffolds. This process revealed a markedly facile aza-Michael-cyclocondensation sequence as a key domino reaction between RCO2NHOH and transient alkylidene Meldrum's acid upon Brønsted base catalysis.

摘要

丙二酸亚异丙酯、羟胺和醛之间发生了前所未有的多组分有机催化的克诺文纳格尔-氮杂-迈克尔-环缩合反应，为大量外消旋和非对映体富集的异恶唑烷酮提供了一条直接的合成途径，这些异恶唑烷酮是具有合成用途的骨架。该过程揭示了在布朗斯特碱催化下，RCO2NHOH与瞬态亚烷基丙二酸亚异丙酯之间的aza-Michael-环缩合序列是一个明显容易发生的关键多米诺反应。