双恶唑啉-路易斯酸催化的N-氧基吡啶醛和酮衍生物的直接电子需求氧杂-杂环狄尔斯-阿尔德反应。

Bisoxazoline-Lewis acid-catalyzed direct-electron demand oxo-hetero-Diels-Alder reactions of N-oxy-pyridine aldehyde and ketone derivatives.

作者信息

Landa Aitor, Richter Bo, Johansen Rasmus Lyng, Minkkilä Anna, Jørgensen Karl Anker

机构信息

Danish National Research Foundation: Center for Catalysis, Department of Chemistry, Aarhus University, DK-8000 Aarhus C, Denmark.

出版信息

J Org Chem. 2007 Jan 5;72(1):240-5. doi: 10.1021/jo062012u.

DOI:10.1021/jo062012u

PMID:17194105

Abstract

A general catalytic oxo-hetero-Diels-Alder reaction for pro-chiral aldehyde and ketone N-oxy-pyridines is presented. The catalytic and asymmetric oxo-hetero-Diels-Alder reaction of electron-rich dienes with N-oxy-pyridine-2-carbaldehyde and ketone derivatives, catalyzed by chiral copper(II)-bisoxazoline complexes, gives optically active six-membered oxygen heterocycles in moderate to good yields and with excellent enantioselectivities.

摘要

本文报道了一种用于前手性醛和酮N-氧化吡啶的通用催化氧杂-杂环狄尔斯-阿尔德反应。在手性铜（II）-双恶唑啉配合物催化下，富电子二烯与N-氧化吡啶-2-甲醛和酮衍生物的催化不对称氧杂-杂环狄尔斯-阿尔德反应，以中等至良好的产率和优异的对映选择性得到光学活性的六元氧杂环。