Issue 14, 2003
From the journal:

Chemical Communications

Addition reactions of O-bound cyclic nickel enolates to α,β-unsaturated ketones†

Juan Cámpora,*a   Celia M. Maya,a   Pilar Palma,a   Ernesto Carmona,a   Claudia Graiffb  and  Antonio Tiripicchiob  

* Corresponding authors

a Instituto de Investigaciones Químicas, Universidad de Sevilla – Consejo Superior de Investigaciones Científicas, c/ Américo Vespucio, s/n, Isla de la Cartuja, 41092 Sevilla, Spain
E-mail: campora@iiq.csic.es
Fax: 34 954460565
Tel: 34 954489555

b Dipartamento di Chimica Generale ed Inorganica, Chimica Analitica, Chimica Fisica, Università di Parma, Parco Area delle Scienze 17/A, I-43100 Parma, Italy
E-mail: tiri@unipr.it
Fax: 0521 905557
Tel: 0521 905432

Abstract

The addition of the O-bound nickel enolates [upper bond 1 start]Ni(C6H4-o-C([double bond, length as m-dash]CHR)O[upper bond 1 end])(dippe) (R = H, 1; R = Me, 2) to α,β-unsaturated ketones proceeds with complete stereoselectivity giving rise to [2 + 4] cycloadducts that can further evolve to generate open-chain, Michael-like products. The stereoselectivity of these reactions suggests a concerted mechanism, through an exo transition state.

Graphical abstract: Addition reactions of O-bound cyclic nickel enolates to α,β-unsaturated ketones

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Article information

DOI
https://doi.org/10.1039/B303062H
Article type
Communication
Submitted
19 Mar 2003
Accepted
29 May 2003
First published
16 Jun 2003

Chem. Commun., 2003, 1742-1743

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Addition reactions of O-bound cyclic nickel enolates to α,β-unsaturated ketones

J. Cámpora, C. M. Maya, P. Palma, E. Carmona, C. Graiff and A. Tiripicchio, Chem. Commun., 2003, 1742 DOI: 10.1039/B303062H

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