Highly stereospecific S(N)2-type displacement of sulfinyl by hydroxy group under Pummerer conditions

被引:27
作者
Bravo, P [1 ]
Zanda, M [1 ]
Zappala, C [1 ]
机构
[1] POLITECN MILAN,DIPARTIMENTO CHIM,CNR,CTR STUDIO SOSTANZE ORGAN NAT,I-20131 MILAN,ITALY
关键词
D O I
10.1016/0040-4039(96)01260-9
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The trifluoroacetic anhydride promoted Pummerer reactions of N-Cbz alpha-amino-alpha-trifluoromethyl-beta-p-tolylsulfinyl methyl butanoates 1b-c occur in a highly stereospecific non-oxidative fashion (d.r. > 98:2), resulting in a S(N)2-lype displacement of the sulfinyl by hydroxy group and providing enantiomerically pure alpha-trifluoromethyl-allo-threonine 2b and -threonine 2c derivatives. Copyright (C) 1996 Elsevier Science Ltd
引用
收藏
页码:6005 / 6006
页数:2
相关论文
共 13 条
  • [1] AMONE A, 1996, J ORG CHEM, V61, P3375
  • [2] AMONE A, 1995, TETRAHEDRON LETT, V36, P7301
  • [3] INTRAMOLECULAR CAPTURE OF PUMMERER REARRANGEMENT INTERMEDIATES .3. INTERRUPTED PUMMERER REARRANGEMENT - CAPTURE OF TRICOORDINATE SULFUR SPECIES GENERATED UNDER PUMMERER REARRANGEMENT CONDITIONS
    BATES, DK
    WINTERS, RT
    PICARD, JA
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (11) : 3094 - 3097
  • [4] BRAVO P, 1988, J CHEM RES-S, P216
  • [5] SYNTHESIS OF OPTICALLY PURE (R)-ALPHA-TRIFLUOROMETHYL-ALANINE AND (S)-ALPHA-TRIFLUOROMETHYL-ALANINE
    BRAVO, P
    CAPELLI, S
    MEILLE, SV
    VIANI, F
    ZANDA, M
    KUKHAR, VP
    SOLOSHONOK, VA
    [J]. TETRAHEDRON-ASYMMETRY, 1994, 5 (10) : 2009 - 2018
  • [6] BRAVO P, 1996, IN PRESS GAZZ CHIM I
  • [7] APPLICATIONS OF SULFOXIDES TO ASYMMETRIC-SYNTHESIS OF BIOLOGICALLY-ACTIVE COMPOUNDS
    CARRENO, MC
    [J]. CHEMICAL REVIEWS, 1995, 95 (06) : 1717 - 1760
  • [8] A NOVEL STEREOSELECTIVE ROUTE TO GAMMA-BUTYROLACTONES
    CASEY, M
    MANAGE, AC
    MURPHY, PJ
    [J]. TETRAHEDRON LETTERS, 1992, 33 (07) : 965 - 968
  • [9] De Lucchi O., 1991, ORG REACTIONS, V40, P157, DOI DOI 10.1002/0471264180.0R040.03
  • [10] DEMUNARI S, 1988, J CHEM RES S, P1701