THE REGIOSELECTIVE AND STEREOSPECIFIC SUBSTITUTION OF UNSYMMETRICAL 1,2-DIOLS USING THE 1,3,2-LAMBDA-5-DIOXAPHOSPHOLANE METHODOLOGY

被引：9
|
作者：
PAUTARDCOOPER, A [1 ]
EVANS, SA [1 ]
机构：
[1] UNIV N CAROLINA,CHEM LABS,CHAPEL HILL,NC 27599
来源：
TETRAHEDRON | 1991年 / 47卷 / 09期
基金：
美国国家科学基金会;
关键词：
D O I：
10.1016/S0040-4020(01)96904-2
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Stereospecific tosylate (-OTs) or azide (N3-) substitution at the C-4 stereocenter of a monosubstituted 1,3,2-lambda-5-dioxaphospholane (the equivalent of the C-2 stereocenter in an unsymmetrical 1,2-diol) is readily achieved by treatment with either p-toluenesulfonic acid (p-TsOH) in tetrahydrofuran solvent or p-TsOH/sodium azide in acetonitrile solvent, respectively.
引用
收藏
页码：1603 / 1610
页数：8
相关论文
共 50 条
  • [31] SOME REACTIONS OF BENZALDEHYDE ACETALS WITH ALKYL-LITHIUM REAGENTS - STEREOSPECIFIC OLEFIN SYNTHESIS FROM 1,2-DIOLS
    HINES, JN
    PEAGRAM, MJ
    THOMAS, EJ
    WHITHAM, GH
    JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1973, (20): : 2332 - 2337
  • [32] Selective xylose hydrogenolysis to 1,2-diols using Co@NC catalysts
    Liang Y.
    Li Z.-J.
    Liu Q.-Y.
    Ma L.-L.
    Ranliao Huaxue Xuebao/Journal of Fuel Chemistry and Technology, 2021, 49 (12): : 1898 - 1910
  • [33] Ruthenium catalyzed oxidation of 1,2-diols to 1,2-diketones using bromamine-T as an oxidizing agent
    Jain, SL
    Sharma, VB
    Sain, B
    SYNTHETIC COMMUNICATIONS, 2005, 35 (03) : 465 - 469
  • [34] HIGHLY STEREOSELECTIVE AND ENANTIOSELECTIVE SYNTHESIS OF ANTI-1,2-DIOLS FROM [(E)-GAMMA-(1,3,2-DIOXABORINANYL)ALLYL]DIISOPINOCAMPHEYLBORANE(1) AND ALDEHYDES
    NARLA, G
    BROWN, HC
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1994, 208 : 296 - ORGN
  • [35] Pb(OAc)4 mediated oxidative cleavage of steroidal unsaturated 1,2-diols:: influence of the angular substitution
    Ferreira, MDR
    Hernando, JIM
    Lena, JIC
    Toupet, L
    Birlirakis, N
    Arseniyadis, S
    TETRAHEDRON LETTERS, 1999, 40 (43) : 7679 - 7682
  • [36] ABSOLUTE-CONFIGURATIONS OF ENANTIOMERIC 1,2-DIHYDROBENZO[B]FLUORANTHENE-TRANS-1,2-DIOLS AND DIASTEREOMERIC 1,2,3,3A-TETRAHYDROBENZO[B]FLUORANTHENE-TRANS-1,2-DIOLS
    YANG, SK
    MUSHTAQ, M
    KAN, LS
    JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (01): : 125 - 129
  • [37] REGIOSELECTIVE AND STEREOSELECTIVE RING-OPENING OF EPOXY ALCOHOLS WITH ORGANO-ALUMINUM COMPOUNDS LEADING TO 1,2-DIOLS
    SUZUKI, T
    SAIMOTO, H
    TOMIOKA, H
    OSHIMA, K
    NOZAKI, H
    TETRAHEDRON LETTERS, 1982, 23 (35) : 3597 - 3600
  • [38] TRICYCLIC 1,3,2-LAMBDA-5,4-LAMBDA-5-DIAZADIPHOSPHETIDINES
    KOZHUSHKO, BN
    SILINA, EB
    DOROSHENKO, VV
    MIKHAILYUCHENKO, NK
    SHOKOL, VA
    ZHURNAL OBSHCHEI KHIMII, 1986, 56 (08): : 1758 - 1763
  • [39] ON DIOXOLANATION REACTION OF CYCLOHEX-3-ENE-1-CARBALDEHYDES WITH 1,2-DIOLS AND PROPERTIES OF PREPARED PRODUCTS
    Kerimov, A. Kh
    Orudzheva, A. T.
    Mamedova, Kh A.
    CHEMICAL PROBLEMS, 2019, (01): : 93 - 99
  • [40] 1,2-LAMBDA(5)-AZAPHOSPHININES AND A NEW 1-LAMBDA(5),3-LAMBDA(5)-.DIPHOSPHININE
    FLUCK, E
    ROSCHE, F
    HECKMANN, G
    WELLER, F
    HETEROATOM CHEMISTRY, 1995, 6 (04) : 355 - 363
12345