ALPHA-HYDROXY KETONES IN HIGH ENANTIOMERIC PURITY FROM ASYMMETRIC DIHYDROXYLATION OF ENOL ETHERS

被引:143
作者
HASHIYAMA, T [1 ]
MORIKAWA, K [1 ]
SHARPLESS, KB [1 ]
机构
[1] Scripps Res Inst, DEPT CHEM, 10666 N TORREY PINES RD, LA JOLLA, CA 92037 USA
关键词
D O I
10.1021/jo00045a011
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Highly enantioselective construction of alpha-hydroxy ketones by the osmium-catalyzed asymmetric dihydroxylation of the corresponding enol ethers has been achieved.
引用
收藏
页码:5067 / 5068
页数:2
相关论文
共 10 条
  • [1] CHEMISTRY OF OXAZIRIDINES .14. ASYMMETRIC OXIDATION OF KETONE ENOLATES USING ENANTIOMERICALLY PURE (CAMPHORYLSULFONYL)OXAZIRIDINE
    DAVIS, FA
    SHEPPARD, AC
    CHEN, BC
    HAQUE, MS
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (18) : 6679 - 6690
  • [2] GIRIJAVALLABHAN VM, 1991, BIOORG MED CHEM LETT, V1, P349, DOI 10.1016/S0960-894X(01)80470-4
  • [3] HANESSIAN S, 1983, TOTAL SYNTHESIS NATU, pCH2
  • [4] CHEMISTRY OF CARBANIONS .18. PREPARATION OF TRIMETHYLSILYL ENOL ETHERS
    HOUSE, HO
    CZUBA, LJ
    GALL, M
    OLMSTEAD, HD
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1969, 34 (08) : 2324 - &
  • [5] ESTER ENOLATE CLAISEN REARRANGEMENT - STEREOCHEMICAL CONTROL THROUGH STEREOSELECTIVE ENOLATE FORMATION
    IRELAND, RE
    MUELLER, RH
    WILLARD, AK
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1976, 98 (10) : 2868 - 2877
  • [6] KONOSU T, 1991, CHEM PHARM BULL, V39, P2241, DOI 10.1248/cpb.39.2241
  • [7] NEW LIGANDS DOUBLE THE SCOPE OF THE CATALYTIC ASYMMETRIC DIHYDROXYLATION OF OLEFINS
    SHARPLESS, KB
    AMBERG, W
    BELLER, M
    CHEN, H
    HARTUNG, J
    KAWANAMI, Y
    LUBBEN, D
    MANOURY, E
    OGINO, Y
    SHIBATA, T
    UKITA, T
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (15) : 4585 - 4588
  • [8] THE OSMIUM-CATALYZED ASYMMETRIC DIHYDROXYLATION - A NEW LIGAND CLASS AND A PROCESS IMPROVEMENT
    SHARPLESS, KB
    AMBERG, W
    BENNANI, YL
    CRISPINO, GA
    HARTUNG, J
    JEONG, KS
    KWONG, HL
    MORIKAWA, K
    WANG, ZM
    XU, DQ
    ZHANG, XL
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (10) : 2768 - 2771
  • [9] REACTIONS OF ESTERS WITH PHOSPHORUS YLIDES .3. DIRECT CONVERSION INTO BRANCHED OLEFINS
    UIJTTEWAAL, AP
    JONKERS, FL
    VANDERGEN, A
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1979, 44 (18) : 3157 - 3168
  • [10] WOHL RA, 1974, SYNTHESIS-STUTTGART, P38