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Catalytic enantioselective conjugate addition of Grignard reagents to cyclic α,β-unsaturated carbonyl compounds

✍ Scribed by Motomu Kanai; Yuichi Nakagawa; Kiyoshi Tomioka

Publisher
Elsevier Science
Year
1999
Tongue
French
Weight
781 KB
Volume
55
Category
Article
ISSN
0040-4020

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✦ Synopsis

A catalytic asymmetric conjugate addition reaction of organocopper reagents, generated from copper salt, a chiral phosphine, and Grignard reagent, with cyclohexenone is highly dependent on the counter anion of copper species, solvents, Grignard reagents, and the structure of the chiral phosphine. The reaction using the combination of 8 mol% of copper iodide, 32 mol% of the amidophosphine 3, and 1.2 equiv of organomagnesium chloride with cyelohexenone in ether at -78 °C gave the 3-substituted cyclohexanune in up to 92% ee and 90% yield.

📜 SIMILAR VOLUMES

ChemInform Abstract: Catalytic Enantiose
ChemInform Abstract: Catalytic Enantioselective Conjugate Addition of Grignard Reagents to Cyclic α,β-Unsaturated Carbonyl Compounds.
✍ Motomu Kanai; Yuichi Nakagawa; Kiyoshi Tomioka 📂 Article 📅 2010 🏛 John Wiley and Sons ⚖ 35 KB 👁 2 views

Catalytic Enantioselective Conjugate Addition of Grignard Reagents to Cyclic α,β-Unsaturated Carbonyl Compounds. -The outcome of the title reaction is influenced by many factors such as amount and structure of the chiral phosphine, copper salt, Grignard reagent, as well as the solvent used.

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The enantioselective copper-catalyzed 1,4-addition of Grignard reagents to a$-unsaturated carbonyl compounds was studied with the following Cu' compounds as catalyst precursor and 1,2 : 5,6-di-0 -isopropylidene-3thio-a -o-glucofuranose (Hsiig) as chiral ligand: CuI, iodo[bis(dibutylsulfide)]copper(I

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