Conjugate addition of mixed diorganozinc compounds and functionalized organozinc cuprates to nitroolefins.

Autor: Rimkus A; University of Bielefeld, Faculty of Chemistry, P.O. Box 10 01 31, Germany., Sewald N
Jazyk: angličtina
Zdroj: Organic letters [Org Lett] 2002 Sep 19; Vol. 4 (19), pp. 3289-91.
DOI: 10.1021/ol026557w
Abstrakt: [reaction: see text] The copper-catalyzed conjugate addition of symmetrical and mixed diorganozinc compounds as well as functionalized diorganozinc cuprates to nitroolefins leads to synthetically versatile nitro compounds in moderate to good yields. Mixed TMSM-organozinc compounds are suitable reagents for conjugate addition, since the TMSM group is not being transferred. Ipso substitution is observed in the absence of a catalytic amount of copper(I) salt. The nitroalkene moiety in 3-nitroacrylates proved to be the predominant Michael acceptor.
Databáze: MEDLINE