A CONCISE, GENERAL ENANTIOSELECTIVE SYNTHETIC ROUTE TO 2(R)-[1'(S)-AZIDO-2-PHENYLETHYL]OXIRANE AND 2(S)-[1'(S)-AZIDO-2-PHENYLETHYL]OXIRANE AND RELATED EPOXIDES

被引:16
作者
BENNETT, F
GIRIJAVALLABHAN, VM
PATEL, N
机构
关键词
D O I
10.1039/c39930000737
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The title oxiranes were constructed in >95% enantiomeric excess (e.e.) utilizing a Sharpless asymmetric epoxidation followed by regioselective azide displacement with [Ti(OPri)2(N3)2] as the key steps.
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页码:737 / 738
页数:2
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共 10 条
  • [1] CARON M, 1988, J ORG CHEM, V53, P5187
  • [2] ALPHA-METHOXY-ALPHA-TRIFLUOROMETHYLPHENYLACETIC ACID, A VERSATILE REAGENT FOR DETERMINATION OF ENANTIOMERIC COMPOSITION OF ALCOHOLS AND AMINES
    DALE, JA
    DULL, DL
    MOSHER, HS
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1969, 34 (09) : 2543 - &
  • [3] A STEREOCONTROLLED SYNTHESIS OF HYDROXYETHYLENE DIPEPTIDE ISOSTERES USING NOVEL, CHIRAL AMINOALKYL EPOXIDES AND GAMMA-(AMINOALKYL) GAMMA-LACTONES
    EVANS, BE
    RITTLE, KE
    HOMNICK, CF
    SPRINGER, JP
    HIRSHFIELD, J
    VEBER, DF
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (23) : 4615 - 4625
  • [4] GHOSH AK, 1992, J CHEM SOC CHEM COMM, P273, DOI 10.1039/C39920000273
  • [5] RENIN INHIBITORS
    GREENLEE, WJ
    [J]. MEDICINAL RESEARCH REVIEWS, 1990, 10 (02) : 173 - 236
  • [6] THE 1ST PRACTICAL METHOD FOR ASYMMETRIC EPOXIDATION
    KATSUKI, T
    SHARPLESS, KB
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1980, 102 (18) : 5974 - 5976
  • [7] A SYNTHESIS OF PROTECTED AMINOALKYL EPOXIDES FROM ALPHA-AMINO-ACIDS
    LULY, JR
    DELLARIA, JF
    PLATTNER, JJ
    SODERQUIST, JL
    YI, N
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (08) : 1487 - 1492
  • [8] SYNTHESIS AND ANTIVIRAL ACTIVITY OF A SERIES OF HIV-1 PROTEASE INHIBITORS WITH FUNCTIONALITY TETHERED TO THE P1 OR P1' PHENYL SUBSTITUENTS - X-RAY CRYSTAL-STRUCTURE ASSISTED DESIGN
    THOMPSON, WJ
    FITZGERALD, PMD
    HOLLOWAY, MK
    EMINI, EA
    DARKE, PL
    MCKEEVER, BM
    SCHLEIF, WA
    QUINTERO, JC
    ZUGAY, JA
    TUCKER, TJ
    SCHWERING, JE
    HOMNICK, CF
    NUNBERG, J
    SPRINGER, JP
    HUFF, JR
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 1992, 35 (10) : 1685 - 1701
  • [9] A SERIES OF POTENT HIV-1 PROTEASE INHIBITORS CONTAINING A HYDROXYETHYL SECONDARY AMINE TRANSITION-STATE ISOSTERE - SYNTHESIS, ENZYME-INHIBITION, AND ANTIVIRAL ACTIVITY
    TUCKER, TJ
    LUMMA, WC
    PAYNE, LS
    WAI, JM
    DESOLMS, SJ
    GIULIANI, EA
    DARKE, PL
    HEIMBACH, JC
    ZUGAY, JA
    SCHLEIF, WA
    QUINTERO, JC
    EMINI, EA
    HUFF, JR
    ANDERSON, PS
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 1992, 35 (14) : 2525 - 2533
  • [10] HIV-1 PROTEASE INHIBITORS BASED ON HYDROXYETHYLENE DIPEPTIDE ISOSTERES - AN INVESTIGATION INTO THE ROLE OF THE P1' SIDE-CHAIN ON STRUCTURE ACTIVITY
    YOUNG, SD
    PAYNE, LS
    THOMPSON, WJ
    GAFFIN, N
    LYLE, TA
    BRITCHER, SF
    GRAHAM, SL
    SCHULTZ, TH
    DEANA, AA
    DARKE, PL
    ZUGAY, J
    SCHLEIF, WA
    QUINTERO, JC
    EMINI, EA
    ANDERSON, PS
    HUFF, JR
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 1992, 35 (10) : 1702 - 1709