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Volumn 125, Issue 11, 2003, Pages 3220-3221

Asymmetric skeletal rearrangement of symmetrically α,α-disubstituted α-amino aldehydes: A new entry to optically active α-hydroxy ketones

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE DERIVATIVE; ALPHA AMINO ACID; ALPHA HYDROXY KETONE DERIVATIVE; KETONE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 0037454306     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0292851     Document Type: Article
Times cited : (39)

References (27)
  • 7
  • 11
    • 0000882040 scopus 로고
    • For asymmetric synthesis of α-hydroxy ketones, see: (a) (asymmetric dihydroxylation of enol ethers) Hashiyama, T.; Morikawa, K.; Sharpless, K. B. J. Org. Chem. 1992, 57, 5067. (b) (asymmetric oxidation of ketone enolates with chiral oxaziridines) Davis, F. A.; Sheppard, A. C.; Chen, B.-C.; Haque, M. S. J. Am. Chem. Soc. 1990, 112, 6679. (c) (asymmetric oxidation of ketones by chiral phase-transfer catalysis) Masui, M.; Ando, A.; Shioiri, T. Tetrahedron Lett. 1988, 29, 2835.
    • (1992) J. Org. Chem. , vol.57 , pp. 5067
    • Hashiyama, T.1    Morikawa, K.2    Sharpless, K.B.3
  • 12
    • 0000227155 scopus 로고
    • For asymmetric synthesis of α-hydroxy ketones, see: (a) (asymmetric dihydroxylation of enol ethers) Hashiyama, T.; Morikawa, K.; Sharpless, K. B. J. Org. Chem. 1992, 57, 5067. (b) (asymmetric oxidation of ketone enolates with chiral oxaziridines) Davis, F. A.; Sheppard, A. C.; Chen, B.-C.; Haque, M. S. J. Am. Chem. Soc. 1990, 112, 6679. (c) (asymmetric oxidation of ketones by chiral phase-transfer catalysis) Masui, M.; Ando, A.; Shioiri, T. Tetrahedron Lett. 1988, 29, 2835.
    • (1990) J. Am. Chem. Soc. , vol.112 , pp. 6679
    • Davis, F.A.1    Sheppard, A.C.2    Chen, B.-C.3    Haque, M.S.4
  • 13
    • 0000359801 scopus 로고
    • For asymmetric synthesis of α-hydroxy ketones, see: (a) (asymmetric dihydroxylation of enol ethers) Hashiyama, T.; Morikawa, K.; Sharpless, K. B. J. Org. Chem. 1992, 57, 5067. (b) (asymmetric oxidation of ketone enolates with chiral oxaziridines) Davis, F. A.; Sheppard, A. C.; Chen, B.-C.; Haque, M. S. J. Am. Chem. Soc. 1990, 112, 6679. (c) (asymmetric oxidation of ketones by chiral phase-transfer catalysis) Masui, M.; Ando, A.; Shioiri, T. Tetrahedron Lett. 1988, 29, 2835.
    • (1988) Tetrahedron Lett. , vol.29 , pp. 2835
    • Masui, M.1    Ando, A.2    Shioiri, T.3
  • 14
    • 0242559561 scopus 로고    scopus 로고
    • note
    • 17 or by the double alkylation of glycine Schiff base.
  • 15
    • 0242644220 scopus 로고    scopus 로고
    • note
    • 2 revealed the formation of the neutral imine 6; thus, the reaction might be driven by coordination of the aluminum on aldehyde carbonyl and the N - H proton abstraction in this case. Equation presented
  • 18
    • 0242475789 scopus 로고    scopus 로고
    • note
    • 18,19 Equation presented
  • 19
    • 0242475788 scopus 로고    scopus 로고
    • note
    • α,α-Disubstituted α-amino aldehydes are stable and easy to handle as compared to α-monosubstituted aldehydes, and, particularly, 2d is generally obtained as a solid with enhanced stability.
  • 22
    • 0242559560 scopus 로고    scopus 로고
    • note
    • 1H NMR analysis after conversion to the oxazolidin-2-one derivative. See the Supporting Information.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.