Regio- and stereoselective ring opening of 2,3-epoxyalcohols with diethylaluminium azide

被引:57
作者
Benedetti, F [1 ]
Berti, F [1 ]
Norbedo, S [1 ]
机构
[1] Univ Trieste, Dipartimento Sci Chim, I-34127 Trieste, Italy
关键词
aluminium and compounds; azides; epoxides; isosteres;
D O I
10.1016/S0040-4039(98)01733-X
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
2,3-Epoxyalcohols react with diethylaluminium azide under mild conditions to give 3-azido-1,2-diols resulting from the regio- and stereoselective attack of the nucleophile at the epoxide C-3. The high regioselectivity (>25:1) observed with both cis and trans substituted epoxides is not affected by bulky substituents at C-3. The method has been successfully applied also to the synthesis of diaminodiol dipeptide isosteres, (C) 1998 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:7971 / 7974
页数:4
相关论文
共 20 条
  • [1] BENEDETTI F, 1997, J ORG CHEM, V62, P9349
  • [2] A convenient synthesis of 1-(S)-[1'-(S)-(t-butyloxycarbonylamino)-2'-phenylethyl]oxirane. A useful building block in the synthesis of HIV protease inhibitors.
    Branalt, J
    Kvarnstrom, I
    Classon, B
    Samuelsson, B
    Nillroth, U
    Danielson, UH
    Karlen, A
    Hallberg, A
    [J]. TETRAHEDRON LETTERS, 1997, 38 (19) : 3483 - 3486
  • [3] CARON M, 1988, J ORG CHEM, V53, P5187
  • [4] A NEW SYNTHESIS FOR ALKYLMETAL AZIDES
    DEHNICKE, K
    STRAHLE, J
    SEYBOLD, D
    MULLER, J
    [J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1966, 6 (03) : 298 - &
  • [5] Jurczak J., 1997, PREPARATIVE CARBOHYD, P595
  • [6] DISCOVERY OF A PEPTIDE-BASED RENIN INHIBITOR WITH ORAL BIOAVAILABILITY AND EFFICACY
    KLEINERT, HD
    ROSENBERG, SH
    BAKER, WR
    STEIN, HH
    KLINGHOFER, V
    BARLOW, J
    SPINA, K
    POLAKOWSKI, J
    KOVAR, P
    COHEN, J
    DENISSEN, J
    [J]. SCIENCE, 1992, 257 (5078) : 1940 - 1943
  • [7] ASYMMETRIC EPOXIDATION OF ALLYL ALCOHOL - EFFICIENT ROUTES TO HOMOCHIRAL BETA-ADRENERGIC BLOCKING-AGENTS
    KLUNDER, JM
    KO, SY
    SHARPLESS, KB
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (19) : 3710 - 3712
  • [8] RENIN INHIBITORS - DIPEPTIDE ANALOGS OF ANGIOTENSINOGEN UTILIZING A DIHYDROXYETHYLENE TRANSITION-STATE MIMIC AT THE SCISSILE BOND TO IMPART GREATER INHIBITORY POTENCY
    LULY, JR
    BAMAUNG, N
    SODERQUIST, J
    FUNG, AKL
    STEIN, H
    KLEINERT, HD
    MARCOTTE, PA
    EGAN, DA
    BOPP, B
    MERITS, I
    BOLIS, G
    GREER, J
    PERUN, TJ
    PLATTNER, JJ
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 1988, 31 (12) : 2264 - 2276
  • [9] A HIGHLY REGIOSELECTIVE AND STEREOSELECTIVE RING-OPENING OF 2,3-EPOXY ALCOHOLS WITH TRIMETHYLSILYL AZIDE-DIETHYLALUMINUM FLUORIDE SYSTEM
    MARUOKA, K
    SANO, H
    YAMAMOTO, H
    [J]. CHEMISTRY LETTERS, 1985, (05) : 599 - 602
  • [10] MEREYALA HB, 1986, HELV CHIM ACTA, V69, P415