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Volumn 65, Issue 4, 2009, Pages 831-843

The asymmetric aminohydroxylation route to GABOB and homoserine derivatives

Author keywords

Amino acid; Asymmetric aminohydroxylation; Asymmetric catalysis; Osmium; Regioselective

Indexed keywords

4 AMINO 3 HYDROXYBUTYRIC ACID; ETHER DERIVATIVE; HYDROXYAMINO ACID;

EID: 57649096934     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2008.11.037     Document Type: Article
Times cited : (16)

References (58)
  • 24
    • 0036381072 scopus 로고    scopus 로고
    • Chirality 14 (2002) 757
    • (2002) Chirality , vol.14 , pp. 757
  • 28
  • 36
    • 0037131291 scopus 로고    scopus 로고
    • The aromatic ethers were prepared from the corresponding phenol and but-3-ene-1-ol under Mitsunobu conditions:
    • The aromatic ethers were prepared from the corresponding phenol and but-3-ene-1-ol under Mitsunobu conditions:. Ramachandran P.V., Chandra J.S., and Reddy M.V.R. J. Org. Chem. 67 (2002) 7547
    • (2002) J. Org. Chem. , vol.67 , pp. 7547
    • Ramachandran, P.V.1    Chandra, J.S.2    Reddy, M.V.R.3
  • 38
    • 57649094628 scopus 로고    scopus 로고
    • note
    • 1H NMR spectrum of crude reaction mixture.
  • 39
    • 57649095471 scopus 로고    scopus 로고
    • note
    • Determined by chiral HPLC using Chiralpak AD or Chiralcel OD-H columns.
  • 43
    • 57649098464 scopus 로고    scopus 로고
    • note
    • -1 more stable than alternate binging modes; See Ref. 2.
  • 44
    • 57649101231 scopus 로고    scopus 로고
    • note
    • Crystallographic data (excluding structure factors) for the structure in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC 701980. Copies of the data can be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK, (fax: +44 (0) 1223-336033 or e-mail: deposit@ccdc.cam.ac.uk). The CIF file is reported as Supplementary data.
  • 45
    • 0001227655 scopus 로고
    • The face-to-face interaction of these electron deficient aromatic units can be rationalised by the Hunter and Sanders model of π-π interactions: For a further discussion of the nature of this interaction see Ref. 2
    • The face-to-face interaction of these electron deficient aromatic units can be rationalised by the Hunter and Sanders model of π-π interactions:. Hunter C.A., and Sanders J.K.M. J. Am. Chem. Soc. 112 (1990) 5525 For a further discussion of the nature of this interaction see Ref. 2
    • (1990) J. Am. Chem. Soc. , vol.112 , pp. 5525
    • Hunter, C.A.1    Sanders, J.K.M.2
  • 46
    • 57649091753 scopus 로고    scopus 로고
    • note
    • -1 lower in energy (MM2/Chem3D Pro) than the corresponding twisted conformation (C2′-C1′-O-C5 dihedral angle 85°, local minimum).
  • 49
    • 57649111416 scopus 로고    scopus 로고
    • note
    • 2PHAL crystal structure: see Ref. 26.
  • 51
    • 57649093714 scopus 로고    scopus 로고
    • note
    • -1 (MM2/Chem 3D Pro) higher in energy than the corresponding extended conformation (C1′-C2′-C3′-C4′ dihedral angle 119°). A similar conformation has been proposed for the Sharpless AD reaction of homoallyl aryl ethers: see Ref. 28.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.