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Volumn , Issue 3, 2005, Pages 461-464

Enantiopure α-silyl-substituted α-hydroxyacetic acids using O-H insertion methodology and boron-based asymmetric reductions

Author keywords

Asymmetric borane reduction; Diazo compounds; Dirhodium(n) acetate; Hydroxy acids; O H insertion

Indexed keywords

ALPHA HYDROXYACETIC ACID; BENZYL 2 SILYL 2 DIAZOACETATE DERIVATIVE; BORANE DERIVATIVE; BORON; GLYCOLIC ACID DERIVATIVE; PHENETHYL ALCOHOL; SALICYLIC ACID BENZYL ESTER; SILANE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 14644392138     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2005-862369     Document Type: Article
Times cited : (18)

References (36)
  • 1
    • 14644429287 scopus 로고    scopus 로고
    • New address: Beiersdorf AG, Unnastr. 48, 20245 Hamburg, Germany
    • New address: Beiersdorf AG, Unnastr. 48, 20245 Hamburg, Germany.
  • 2
    • 14644419810 scopus 로고    scopus 로고
    • New address: ProBioGen AG, Goethestr. 50-54, 13086 Berlin, Germany
    • New address: ProBioGen AG, Goethestr. 50-54, 13086 Berlin, Germany.
  • 21
    • 14644409345 scopus 로고    scopus 로고
    • note
    • 3): δ = 0.9, 1.1, 5.7, 6.0, 6.1, 23.0, 64.7, 68.7, 78.0, 125.3, 125.8, 126.0, 126.5, 127.0, 127.1, 127.2, 134.8, 141.5, 172.6.
  • 23
    • 0009241088 scopus 로고    scopus 로고
    • Ramachandran, P. V.; Brown, H. C., Eds.; ACS Symposium Series 783, American Chemical Society: Washington DC
    • (b) Cho, B. T.; Chun, Y. S. In Organoboranes for Synthesis; Ramachandran, P. V.; Brown, H. C., Eds.; ACS Symposium Series 783, American Chemical Society: Washington DC, 2001, 122.
    • (2001) Organoboranes for Synthesis , pp. 122
    • Cho, B.T.1    Chun, Y.S.2
  • 33
    • 14644444769 scopus 로고    scopus 로고
    • note
    • 2 solution (67 μL) were simultaneously added. The reaction mixture was left stirring in an ice bath for 2.5 h. Flash column chromatography on silica gel (15:1 hexane-EtOAc) afforded benzyl 2-triethylsilyl-2-hydroxyacetate (2b) as a colorless oil in 71% yield (54 mg) and 91% ee (for the details of the ee-determination see footnote b in Table 2).
  • 34
    • 14644391135 scopus 로고    scopus 로고
    • note
    • 19 for the structure shown in Figure 2. The hydrogen positions could be located and have been refined isotropically. The crystal structure of (R)-3c has been deposited as supplementary publication no. CCDC 255777 at the Cambridge Crystallographic Data Centre. Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK [fax: +44(1223)336033; e-mail: deposit@ccdc.cam.ac.uk, or http//www.ccdc.cam.ac.uk].


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.