Issue 27, 2013
From the journal:

Organic & Biomolecular Chemistry

Enantioselective Mukaiyama–Michael with 2-enoyl pyridine N-oxides catalyzed by PYBOX-DIPH-Zn(ii)-complexes at ambient temperature†‡

Subhrajit Rout,a   Sumit K. Rayb  and  Vinod K. Singh*ab  

* Corresponding authors

a Department of Chemistry, Indian Institute of Science Education and Research Bhopal, Bhopal, M.P. 460 023, India

b Department of Chemistry, Indian Institute of Technology Kanpur, Kanpur, UP 208 016, India
E-mail: vinodks@iitk.ac.in
Fax: (+)91-755-4092392

Abstract

A chiral PYBOX-DIPH-Zn(II) catalyzed enantioselective Mukaiyama–Michael reaction of acyclic silyl enol ethers with 2-enoylpyridine N-oxides has been studied in external additive free conditions at ambient temperature. The methodology offers straightforward access to a variety of functionalized chiral 1,5-dicarbonyl compounds, which could easily be elaborated into synthetically viable pyrones via hydrolysis followed by cyclization. A transition state model has been proposed to explain the stereochemical outcome.

Graphical abstract: Enantioselective Mukaiyama–Michael with 2-enoyl pyridine N-oxides catalyzed by PYBOX-DIPH-Zn(ii)-complexes at ambient temperature

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Article information

DOI
https://doi.org/10.1039/C3OB40445E
Article type
Paper
Submitted
05 Mar 2013
Accepted
13 May 2013
First published
31 May 2013

Org. Biomol. Chem., 2013,11, 4537-4545

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Enantioselective Mukaiyama–Michael with 2-enoyl pyridine N-oxides catalyzed by PYBOX-DIPH-Zn(II)-complexes at ambient temperature

S. Rout, S. K. Ray and V. K. Singh, Org. Biomol. Chem., 2013, 11, 4537 DOI: 10.1039/C3OB40445E

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