Unveiling the Mg(ii) promoted [3+2] cycloaddition reaction of mesitonitrile oxide to Baylis–Hilman adduct from the molecular electron density theory perspective

Author:

Domingo Luis R.1ORCID,Acharjee Nivedita2ORCID

Affiliation:

1. Department of Organic Chemistry, University of Valencia, Dr Moliner 50, Burjassot, E-46100 Valencia, Spain

2. Department of Chemistry, Durgapur Government College, J. N. Avenue, Durgapur, West Bengal 713214, India

Abstract

The presence of Mg(ii) cation does not substantially accelerate this low polar zw-type [3+2] cycloaddition reaction, but changes the facial diastereoselectivity. These low polar reactions are completely ortho regioselective.

Funder

Ministerio de Ciencia e Innovación

Publisher

Royal Society of Chemistry (RSC)

Subject

Materials Chemistry,General Chemistry,Catalysis

Reference63 articles.

1. P.Caramella and P.Griinanger , in 1.3-Dipolar Cycloaddition Chemistry , ed. A. Padwa , John Wiley & Sons , New York , 1984 , vol. 3, pp. 291–393

2. K. B. G.Torssell , Nitrile Oxides, Nitrones and Nitronates in Organic Syntesis, Novel Strategies in Synthesis , Wiley-VCH , New York , 2008

3. The Chemistry of the 2-Isoxazolines: Reductive Cleavages

4. First Successful Metal Coordination Control in 1,3-Dipolar Cycloadditions. High-Rate Acceleration and Regio- and Stereocontrol of Nitrile Oxide Cycloadditions to the Magnesium Alkoxides of Allylic and Homoallylic Alcohols

5. Reversal of stereoselectivity of Mg(II) catalysed 1,3-dipolar cycloaddition. Acceleration of cycloaddition by microwave irradiation

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