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Volumn 56, Issue 15, 2000, Pages 2153-2166

Highly chemoselective catalytic hydrogenation of unsaturated ketones and aldehydes to unsaturated alcohols using phosphine-stabilized copper(I) hydride complexes

Author keywords

Carbonyl compounds; Catalysis; Copper and compounds; Hydrogenation

Indexed keywords

ALCOHOL DERIVATIVE; ALDEHYDE; COPPER CHLORIDE; COPPER COMPLEX; KETONE; PHOSPHINE DERIVATIVE; SODIUM DERIVATIVE;

EID: 0034616210     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(99)01098-4     Document Type: Conference Paper
Times cited : (137)

References (94)
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    • The stereochemical preference for axial delivery of hydride represents the kinetic selectivity of the catalytic reduction: the stereoisomeric tripod-stabilized copper(I)-cis-4-tert-butylcyclohexoxide complex, generated independently by treatment of the corresponding potassium alkoxide with (tripod)CuCl, shows no stereomutation to the thermodynamically favored trans-isomer in solution at room temperature.
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    • The rate attenuation observed for the reduction of cyclopentanone substrates is consistent with that observed for sodium borohydride reductions of cyclopentanones versus cyclohexanones. See, for example, Ref. 36.
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    • Control experiments were performed by the addition of an allyl alcohol (e.g. geraniol) to a reaction mixture of a working hydrogenation reaction, subjecting the allylic alcohol to all catalysts and catalyst-derived intermediates present during an active reduction.
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