Synthesis 2005(13): 2239-2245  
DOI: 10.1055/s-2005-870000
PAPER
© Georg Thieme Verlag Stuttgart · New York

Diastereoselective Michael Additions of Chelated Enolates towards Nitroalkenes

Barbara Mendler, Uli Kazmaier*
Institut für Organische Chemie, Universität des Saarlandes, Postfach 151150, 66041 Saarbrücken, Germany
Fax: +49(681)3022409; e-Mail: u.kazmaier@mx.uni-saarland.de;
Further Information

Publication History

Received 25 February 2005
Publication Date:
13 July 2005 (online)

Abstract

Highly reactive chelated enolates are versatile nucleophiles that underwent Michael additions towards nitroalkenes. The yields and selectivities obtained depend on the protecting groups and metal salts used. Zinc enolates in general give the best yields and the selectivities are high with tosylated glycinates. The best selectivities are obtained using tin enolates in combination with the TFA-protecting groups.