Regioselective 1,4-conjugate addition of Grignard reagents to nitrodienes in the presence of catalytic amounts of Zn(II) salts.

Autor: Dhakal RC; Hunter Laboratory, Department of Chemistry, Clemson University , Clemson, South Carolina 29634-0973, United States., Dieter RK
Jazyk: angličtina
Zdroj: Organic letters [Org Lett] 2014 Mar 07; Vol. 16 (5), pp. 1362-5. Date of Electronic Publication: 2014 Feb 19.
DOI: 10.1021/ol500114m
Abstrakt: Grignard reagents undergo facile regioselective 1,4-conjugate addition to nitrodienes in the presence of catalytic amounts of Zn(II) salts with excellent yields. A wide range of ligands such as alkyl, aryl, heteroaryl, allyl, vinyl, 1-alkynyl, and alkoxy ligands were transferred, while a thiolate ligand afforded 1,6-regioselectivity. The reactions were successfully carried out on δ-alkyl- or aryl-substituted α,β,γ,δ-diunsaturated nitrodiene substrates. Regioselectivity is minimally influenced by temperature or choice of solvent.
Databáze: MEDLINE