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Volumn 43, Issue 41, 2002, Pages 7441-7444

Stereoselective reduction of enaminones to syn γ-aminoalcohols

Author keywords

[No Author keywords available]

Indexed keywords

2 N (ISOPROPYLAMINO) 6 METHYL 4 HEPTANOL; 3 N (ETHYLAMINO) 1 PHENYL 1 BUTANOL; 3 N (ISOPROPYLAMINO) 1 PHENYL 1 BUTANOL; 3 N (ISOPROPYLAMINO) 1 PHENYL 5 METHYL 1 HEXANOL; 3 N (METHYLAMINO) 1 PHENYL 1 BUTANOL; 3 N (METHYLAMINO) 1 PHENYL 4 METHYL 1 PENTANOL; 3 N (METHYLAMINO) 1 PHENYL 5 METHYL 1 HEXANOL; 3 N (TERT BUTYLAMINO) 1 PHENYL 1 BUTANOL; 3 PIPERIDINYL 1 PHENYL 1 BUTANOL; AMINO 1 PHENYL 1 BUTANOL; AMINOALCOHOL; UNCLASSIFIED DRUG;

EID: 0037038028     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(02)01545-9     Document Type: Article
Times cited : (18)

References (39)
  • 4
    • 0001222924 scopus 로고
    • Knapp S. Chem. Rev. 95:1995;1859-1876.
    • (1995) Chem. Rev. , vol.95 , pp. 1859-1876
    • Knapp, S.1
  • 31
    • 0011260524 scopus 로고    scopus 로고
    • 3/MeOH, 95:5) gave diastereoisomeric mixture of syn and anti γ-aminoalcohols as pale yellow syrups.
    • 3/MeOH, 95:5) gave diastereoisomeric mixture of syn and anti γ-aminoalcohols as pale yellow syrups.
  • 32
    • 0011260346 scopus 로고    scopus 로고
    • note
    • Abstract.
  • 35
    • 0011262436 scopus 로고    scopus 로고
    • +] typical of a carbonyl compound rather than of an allyl alcohol.
    • +] typical of a carbonyl compound rather than of an allyl alcohol.
  • 36
    • 0011343281 scopus 로고    scopus 로고
    • In our opinion, the formation of an enol ester borohydride intermediate in analogy with the reported reductions of enaminoesters and β-hydroxybenzyl oximes cannot be invoked. This intermediate should transfer hydride to the carbon-carbon double bond, but this double bond appears electrophilic rather than nucleophilic. Alternatively boron could link in the α-position giving rise to a β-enaminoketone, whose reduction can occur either intramolecularly or intermolecularly as in the β-hydroxyketone system. Finally the water molecule, which seems to be present also in 'dry' cerium chloride could be the proton source which allows keto-enol tautomerism, followed by reduction of the β-enaminoketone. Intramolecular shift of a hydrogen atom from nitrogen to oxygen atom is discarded because reduction occurs also with N,N-dialkylamino derivatives (entry 8).
    • In our opinion, the formation of an enol ester borohydride intermediate in analogy with the reported reductions of enaminoesters and β-hydroxybenzyl oximes cannot be invoked. This intermediate should transfer hydride to the carbon-carbon double bond, but this double bond appears electrophilic rather than nucleophilic. Alternatively boron could link in the α-position giving rise to a β-enaminoketone, whose reduction can occur either intramolecularly or intermolecularly as in the β-hydroxyketone system. Finally the water molecule, which seems to be present also in 'dry' cerium chloride could be the proton source which allows keto-enol tautomerism, followed by reduction of the β-enaminoketone. Intramolecular shift of a hydrogen atom from nitrogen to oxygen atom is discarded because reduction occurs also with N,N-dialkylamino derivatives (entry 8).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.