Issue 24, 2000
From the journal:

Chemical Communications

Asymmetric chemo- and regiospecific addition of organozinc reagents to Baylis–Hillman derived allylic electrophiles

Christoph Börner,a   Josep Gimeno,b   Serafino Gladiali,c   Paul J. Goldsmith,a   Daniela Ramazzottic  and  Simon Woodward*a  

* Corresponding authors

a School of Chemistry, Nottingham University, University Park, Nottingham, UK
E-mail: simon.woodward@nottingham.ac.uk
Fax: (+44) 115-9513564
Tel: (+44) 115-9513564

b Departament de Química, Universitat Autònoma de Barcelona, Bellaterra, Barcelona, Spain

c Dipartimento di Chimica, Università di Sassari, Via Vienna 2, Sassari, Italy

Abstract

The copper-catalysed SN2′ addition of ZnR2 to allylic (Z)-ArCH[double bond, length half m-dash]C(CH2X)(CO2Et) (X = Br, Cl, OSO2Me) fashions only ArCH(R)C([double bond, length half m-dash]CH2)(CO2Et); use of a chiral ligand gives up to 64% ee for this demanding reaction.

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Article information

DOI
https://doi.org/10.1039/B006943O
Article type
Communication
Submitted
21 Aug 2000
Accepted
23 Oct 2000
First published
22 Nov 2000

Chem. Commun., 2000, 2433-2434

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Asymmetric chemo- and regiospecific addition of organozinc reagents to Baylis–Hillman derived allylic electrophiles

C. Börner, J. Gimeno, S. Gladiali, P. J. Goldsmith, D. Ramazzotti and S. Woodward, Chem. Commun., 2000, 2433 DOI: 10.1039/B006943O

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