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Volumn 14, Issue 13, 2003, Pages 1763-1766

Enantioselective addition of diethylzinc to aldehydes catalyzed by a β-amino alcohol derived from (+)-3-carene

Author keywords

[No Author keywords available]

Indexed keywords

1 (2 METHOXYPHENYL) 1 PROPANOL; 3 CARENE; ALDEHYDE DERIVATIVE; AMINOALCOHOL; DIETHYLZINC; LIGAND; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; PROPANOL; UNCLASSIFIED DRUG;

EID: 0037756810     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(03)00347-1     Document Type: Article
Times cited : (41)

References (35)
  • 4
    • 0035263817 scopus 로고    scopus 로고
    • Asymmetric Catalysis in Organic Synthesis; Noyori
    • Pu L., Yu H.B. Chem. Rev. 101:2001;757-824 Asymmetric Catalysis in Organic Synthesis; Noyori, R., Ed.; John Wiley & Sons: New York, NY, 1995.
    • (2001) Chem. Rev. , vol.101 , pp. 757-824
    • Pu, L.1    Yu, H.B.2
  • 32
    • 85031152890 scopus 로고    scopus 로고
    • note
    • 4 and evaporation under reduced pressure yielded a crude alcohol, which was further purified by flash column chromatography (acetone/pet ether 1:25) to give the purified alcohols (yield 68%). The enantiomeric excess and absolute configuration was determined from the specific rotation of the purified product.
  • 35
    • 85031151256 scopus 로고    scopus 로고
    • To study the effect of bulk of the N-alkyl substituent on enantioselectivity, (1S,3R,4S,6R)-4-allylamino-3-caranol, a chiral catalyst with less bulkier N-allyl group was synthesized. When used as a chiral catalyst in the enantioselective alkylation of benzaldehyde, (R)-1-phenyl-1-propanol was obtained with 60% ee which is considerably less for the same reaction with chiral catalyst 2 (ee 81% with benzaldehyde)
    • To study the effect of bulk of the N-alkyl substituent on enantioselectivity, (1S,3R,4S,6R)-4-allylamino-3-caranol, a chiral catalyst with less bulkier N-allyl group was synthesized. When used as a chiral catalyst in the enantioselective alkylation of benzaldehyde, (R)-1-phenyl-1-propanol was obtained with 60% ee which is considerably less for the same reaction with chiral catalyst 2 (ee 81% with benzaldehyde).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.