Conjugate Addition of Mixed Diorganozinc Compounds and Functionalized Organozinc Cuprates to Nitroolefins
- 29 August 2002
- journal article
- letter
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 4 (19) , 3289-3291
- https://doi.org/10.1021/ol026557w
Abstract
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.Keywords
This publication has 10 references indexed in Scilit:
- Enantioselective Copper-Catalyzed Conjugate Addition of Dialkyl Zinc to Nitro-OlefinsOrganic Letters, 2000
- Enantioselective copper(I) catalyzed 1,4-addition of diethylzinc to nitroolefinsTetrahedron: Asymmetry, 1998
- Acceleration of the conjugate addition of diethyl zinc to enones by either Cu(OTf)2 or trivalent phosphorus ligandsTetrahedron Letters, 1997
- Gas‐Phase Reaction of Tetraborane(10) with Allene: The Fluxional arachno‐1‐Carbapentaborane(10) Isomeric System and Derivatives 1,2‐ and 1,3‐Me2‐1‐CB4H8; Analogies in 1‐CB4H10, MeB5H10, and B5HAngewandte Chemie International Edition in English, 1997
- Preparation of Functionalized Dialkylzincs via a Boron−Zinc Exchange. Reactivity and Catalytic Asymmetric Addition to AldehydesThe Journal of Organic Chemistry, 1996
- β-Silyl Organocuprates: The Grail of Organocuprate Chemistry?1aJournal of the American Chemical Society, 1996
- Preparation and reactions of polyfunctional organozinc reagents in organic synthesisChemical Reviews, 1993
- Preparation of functionalized dialkylzinc reagents via an iodine-zinc exchange reaction. Highly enantioselective synthesis of functionalized secondary alcoholsThe Journal of Organic Chemistry, 1992
- Synthesis and reactivity toward acyl chlorides and enones of the new highly functionalized copper reagents RCu(CN)ZnIThe Journal of Organic Chemistry, 1988
- Nucleophilic attacks on carbon-carbon double bonds. 31. Complete and partial stereoconversion in vinylic substitution of (E)- and (Z)-.beta.-chloro-.alpha.-phenylcinnamaldehydes and (E)-2-iodo-1,2-diphenyl-1-nitroethylene by nucleophilesThe Journal of Organic Chemistry, 1985