Zinc Metal-Promoted Stereoselective Olefination of Aldehydes and Ketones with gem-Dichloro Compounds in the Presence of Chlorotrimethylsilane
- 1 November 1998
- journal article
- Published by Oxford University Press (OUP) in Bulletin of the Chemical Society of Japan
- Vol. 71 (11) , 2669-2672
- https://doi.org/10.1246/bcsj.71.2669
Abstract
A combination of zinc metal and a catalytic amount of chlorotrimethylsilane has been found to promote the transformation of various aldehydes and ketones with gem-dichloro compounds, such as benzylidene dichloride (1a) and methyl dichloroacetate (1b), to the corresponding cross-coupling products, such as substituted styrene 3 and methyl acrylates 4 derivatives, under mild reaction conditions in THF. The E-isomer of the corresponding alkenes was obtained stereoselectively in good-to-excellent yields. The reaction serves as a very convenient one-pot procedure.This publication has 13 references indexed in Scilit:
- Stereoselective Olefination of Carbonyl Compounds with N-Benzyl- and N-Allylbenzotriazoles by Low-Valent Titanium-Promoted DehydroxybenzotriazolylationThe Journal of Organic Chemistry, 1997
- A Dramatic Effect of a Catalytic Amount of Lead on the Simmons-Smith Reaction and Formation of Alkylzinc Compounds from Iodoalkanes. Reactivity of Zinc Metal: Activation and DeactivationThe Journal of Organic Chemistry, 1994
- A Novel Catalytic Effect of Lead on the Reduction of a Zinc Carbenoid with Zinc Metal Leading to a Geminal Dizinc Compound. Acceleration of the Wittig-Type Olefination with the RCHX2-TiCl4-Zn Systems by Addition of LeadThe Journal of Organic Chemistry, 1994
- Chemistry of and with Highly Reactive MetalsAngewandte Chemie International Edition in English, 1993
- Fluorine-containing organozinc reagents - VI. The preparation of α-Trifluoromethyl-α,β-unsaturated carboxylic acid estersTetrahedron Letters, 1991
- A new method for carbon-carbon double bond formation promoted by tri-n-butylphosphine and zincTetrahedron Letters, 1988
- Activation of zinc by trimethylchlorosilane. An improved procedure for the preparation of .beta.-hydroxy esters from ethyl bromoacetate and aldehydes or ketones (Reformatsky reaction)The Journal of Organic Chemistry, 1987
- METHYLENATION OF CARBONYL COMPOUNDS: (+)-3-METHYLENE-cis-p-METHANEOrganic Syntheses, 1987
- The Wittig Reaction Using Potassium-tert-butoxide High Yield Methylenations of Sterically Hindered KetonesSynthetic Communications, 1985
- Wittig-type Reaction of Dimetallated Carbodianion Species as Produced by Zinc Reduction of gem-Polyhalogen Compounds in the Presence of Lewis AcidsBulletin of the Chemical Society of Japan, 1980