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Volumn 4, Issue 5, 2002, Pages 835-838

Asymmetric synthesis of β-amino alcohols by reductive cross-coupling of benzylideneamine with planar chiral benzaldehydes

Author keywords

[No Author keywords available]

Indexed keywords

AMINE; AMINOALCOHOL; BENZALDEHYDE DERIVATIVE; BENZYLIDENE DERIVATIVE; CROSS LINKING REAGENT;

EID: 0037035038     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0255256     Document Type: Article
Times cited : (32)

References (48)
  • 1
    • 0034697199 scopus 로고    scopus 로고
    • For representative reviews: (a) Bergmeier, S. C. Tetrahedron 2000, 56, 2561.
    • (2000) Tetrahedron , vol.56 , pp. 2561
    • Bergmeier, S.C.1
  • 5
  • 8
    • 0012180631 scopus 로고
    • Asymmetric catalysis via chiral metal complexes
    • John Wiley and Sons: Chichester
    • (h) Noyori, R. Asymmetric Catalysis via Chiral Metal Complexes. In Asymmetric Catalysis in Organic Synthesis; John Wiley and Sons: Chichester, 1994.
    • (1994) Asymmetric Catalysis in Organic Synthesis
    • Noyori, R.1
  • 31
    • 33845281646 scopus 로고
    • An intermolecular cross-coupling between carbonyls and imines for synthesis of β-amino alcohols: (a) Roskamp, E. J.; Pedersen, S. F. J. Am. Chem. Soc. 1987, 109, 6551.
    • (1987) J. Am. Chem. Soc. , vol.109 , pp. 6551
    • Roskamp, E.J.1    Pedersen, S.F.2
  • 38
    • 0025327459 scopus 로고
    • The coordination of a tricarbonylchromium fragment to the arene ring was found to also increase the diastereoselectivity in the asymmetric allylboration of aromatic aldehydes: Roush, W. R.; Park, J. C. J. Org. Chem. 1990, 55, 1143.
    • (1990) J. Org. Chem. , vol.55 , pp. 1143
    • Roush, W.R.1    Park, J.C.2
  • 39
    • 0000192115 scopus 로고
    • Authentic stereodefined anti-N-tosyl-2-amino-1,2-diphenylethyl alcohol derivative was prepared by the following literature procedure: (a) Davis, F. A.; Hague, M. S.; Przeslawski, R. M. J. Org. Chem. 1989, 54, 2021.
    • (1989) J. Org. Chem. , vol.54 , pp. 2021
    • Davis, F.A.1    Hague, M.S.2    Przeslawski, R.M.3
  • 42
    • 85034525324 scopus 로고    scopus 로고
    • Similarly, the cross-coupling of N-tosyl ferrocenylideneamine (1) with benzaldehydes or the corresponding chromium complexes gave exclusively anti-β-amino alcohols under the same conditions: unpublished results
    • Similarly, the cross-coupling of N-tosyl ferrocenylideneamine (1) with benzaldehydes or the corresponding chromium complexes gave exclusively anti-β-amino alcohols under the same conditions: unpublished results.
  • 43
    • 85034526552 scopus 로고    scopus 로고
    • A homo-coupling 1,2-diol was in 80% yield as a major product
    • A homo-coupling 1,2-diol was in 80% yield as a major product.
  • 45
    • 85034528322 scopus 로고    scopus 로고
    • Optical purities of 11 and chromium-free 12 were determined by chiral HPLC. For racemic 11: chiralcel OD-H, hexane/2-propanol (9/1), flow rate 0.5 mL/min, 40°C, retention time 33.1 and 36.0 min. For racemic 12: chiralcel OJ-H, hexane/2-propanol (9/1), flow rate 0.5 mL/min. 40°C, retention time 20.4 and 25.0 min
    • Optical purities of 11 and chromium-free 12 were determined by chiral HPLC. For racemic 11: chiralcel OD-H, hexane/2-propanol (9/1), flow rate 0.5 mL/min, 40°C, retention time 33.1 and 36.0 min. For racemic 12: chiralcel OJ-H, hexane/2-propanol (9/1), flow rate 0.5 mL/min. 40°C, retention time 20.4 and 25.0 min.
  • 46
    • 85034525502 scopus 로고    scopus 로고
    • The absolute configuration of the syn-coupling product 12 was determined as (R,R)-configuration by comparison of the optical rotation sign of authentic syn-β-amino alcohol derived from (R)-2-phenylglycine according to ref 8c
    • The absolute configuration of the syn-coupling product 12 was determined as (R,R)-configuration by comparison of the optical rotation sign of authentic syn-β-amino alcohol derived from (R)-2-phenylglycine according to ref 8c.
  • 48
    • 0000178635 scopus 로고
    • Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon: Oxford
    • (b) Davies, S. G.; McCarthy, T. D. Comprehensive Oragnometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon: Oxford, 1995; Vol. 12, p 1039.
    • (1995) Comprehensive Oragnometallic Chemistry II , vol.12 , pp. 1039
    • Davies, S.G.1    McCarthy, T.D.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.