CHIRAL PYRIDYL ALCOHOL-PROMOTED HIGHLY ENANTIOSELECTIVE AND RAPID ADDITION OF DIALKYLZINC TO PYRIDINECARBOXALDEHYDES

被引:18
作者
ISHIZAKI, M [1 ]
HOSHINO, O [1 ]
机构
[1] SCI UNIV TOKYO, FAC PHARMACEUT SCI, SHINJUKU KU, TOKYO 162, JAPAN
关键词
D O I
10.1246/cl.1994.1337
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Optically active 1-(2-, 3-, and 4-pyridyl)propanols and 1-(3-pyridyl)ethanol were synthesized in good to high enantiomeric excesses (up to 88% e.e.) and in a short reaction time by catalyzed asymmetric addition of dialkylzinc to pyridine-2-, 3- and 4-carboxaldehydes and 6-bromopyridine-2-carboxaldehyde in the presence of tridentate chiral 2-[2,2-dimethyl-1-(2-pyridyl)propoxy]-1,1-diarylethanols.
引用
收藏
页码:1337 / 1340
页数:4
相关论文
共 23 条
  • [1] OPTICALLY-ACTIVE BIPYRIDINES IN ASYMMETRIC CATALYSIS
    BOLM, C
    ZEHNDER, M
    BUR, D
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1990, 29 (02): : 205 - 207
  • [2] ENANTIOSELECTIVE SYNTHESIS OF OPTICALLY-ACTIVE PYRIDINE-DERIVATIVES AND C-2-SYMMETRICAL 2,2'-BIPYRIDINES
    BOLM, C
    EWALD, M
    FELDER, M
    SCHLINGLOFF, G
    [J]. CHEMISCHE BERICHTE-RECUEIL, 1992, 125 (05): : 1169 - 1190
  • [3] SELECTIVE REDUCTIONS .46. EFFECT OF THE STERIC REQUIREMENT AT THE 2-POSITION OF APOPINENE ON CHIRAL REDUCTIONS - B-(ISO-2-ETHYLAPOPINOCAMPHEYL)-9-BORABICYCLO[3.3.1]NONANES AND B-(ISO-2-N-PROPYLAPOPINOCAMPHEYL)-9-BORABICYCLO[3.3.1]NONANES AS IMPROVED REAGENTS FOR THE CHIRAL REDUCTION OF ALPHA,BETA-ACETYLENIC KETONES AND ALPHA-KETO ESTERS
    BROWN, HC
    RAMACHANDRAN, PV
    WEISSMAN, SA
    SWAMINATHAN, S
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (26) : 6328 - 6333
  • [4] CHIRAL LIGANDS CONTAINING HETEROATOMS .8. 2-[(2S)-2-PYRROLIDINYL]PYRIDINE AS A NOVEL CATALYST IN THE ENANTIOSELECTIVE ADDITION OF DIETHYLZINC TO ALDEHYDES
    CHELUCCI, G
    CONTI, S
    FALORNI, M
    GIACOMELLI, G
    [J]. TETRAHEDRON, 1991, 47 (38) : 8251 - 8258
  • [5] CHELUCCI G, 1992, TETRAHEDRON, V48, P8993
  • [6] KINETIC RESOLUTION OF RACEMIC CARBOXYLIC-ACIDS WITH HOMOCHIRAL ALCOHOLS AND DICYCLOHEXYLCARBODIIMIDE
    CHINCHILLA, R
    NAJERA, C
    YUS, M
    HEUMANN, A
    [J]. TETRAHEDRON-ASYMMETRY, 1991, 2 (02) : 101 - 104
  • [7] ASYMMETRIC-SYNTHESIS AND ABSOLUTE STEREOCHEMISTRY OF LY248686
    DEETER, J
    FRAZIER, J
    STATEN, G
    STASZAK, M
    WEIGEL, L
    [J]. TETRAHEDRON LETTERS, 1990, 31 (49) : 7101 - 7104
  • [8] FALORNI M, 1992, GAZZ CHIM ITAL, V122, P339
  • [9] SYNTHESIS OF 1S,2R,3S,4R,5R-METHYL[2,3,4-TRIHYDROXY-5-(HYDROXYMETHYL)CYCLOPENTYL]AMINE - A POTENT ALPHA-MANNOSIDASE INHIBITOR
    FARR, RA
    PEET, NP
    KANG, MS
    [J]. TETRAHEDRON LETTERS, 1990, 31 (49) : 7109 - 7112
  • [10] OPTICALLY-ACTIVE NAPROXEN BY KINETIC RESOLUTION
    FRANCK, A
    RUCHARDT, C
    [J]. CHEMISTRY LETTERS, 1984, (08) : 1431 - 1434