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Me3SiCl accelerated conjugate addition of stoichiometric organocopper reagents

โœ Scribed by Eiichi Nakamura; Satoshi Matsuzawa; Yoshiaki Horiguchi; Isao Kuwajima

Publisher
Elsevier Science
Year
1986
Tongue
French
Weight
302 KB
Volume
27
Category
Article
ISSN
0040-4039

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โœฆ Synopsis

Chlorotrimethylsilane, particularly if combined with hexamethylphosphoric triamide or 4_dimethylaminopyridine, strongly promote the conjugate addition of stoichiometric organocopper reagents.

๐Ÿ“œ SIMILAR VOLUMES

Me3SiCl/HMPA accelerated conjugate addit
Me3SiCl/HMPA accelerated conjugate addition of catalytic copper reagent. Stereoselective synthesis of enol silyl ether of aldehyde
โœ Yoshiaki Horiguchi; Satoshi Matsuzawa; Eiichi Nakamura; Isao Kuwajima ๐Ÿ“‚ Article ๐Ÿ“… 1986 ๐Ÿ› Elsevier Science ๐ŸŒ French โš– 277 KB

Copper-catalyzed conjugate addition of the Grignard reagents in the presence of Me3SiCl and HMPA proceeds in much higher yield than the reaction of conventional organocopper reagents and shows very good regio-, stereo-, and chemoselectivities. Conjugate addition of organocopper reagents,' originated

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Mediated by a noncovalently bound chiral amidophosphine iigand I, reaction of organocoppers with cycloalkenones 2 aforded the corresponding J-substituted cyclo-aLk-anones 3 in 9568% ee.