Practical synthesis of enantiopure cyclic 1,2-amino alcohols via catalytic asymmetric ring opening of meso epoxides

被引:139
作者
Schaus, SE [1 ]
Larrow, JF [1 ]
Jacobsen, EN [1 ]
机构
[1] HARVARD UNIV,DEPT CHEM & BIOL CHEM,CAMBRIDGE,MA 02138
关键词
D O I
10.1021/jo970146p
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
引用
收藏
页码:4197 / 4199
页数:3
相关论文
共 18 条
  • [1] AGER DJ, 1996, CHEM REV, V96, P8350
  • [2] REACTION OF TRANS-2-ACYLAMINOCYCLANOLS WITH THIONYL CHLORIDE
    BANNARD, RAB
    GIBSON, NCC
    PARKKARI, JH
    [J]. CANADIAN JOURNAL OF CHEMISTRY, 1971, 49 (12): : 2064 - &
  • [3] PREPARATION AND ABSOLUTE-CONFIGURATION OF TRANS-2-AMINOCYCLOPENTANOL ENANTIOMERS
    BARR, AA
    FRENCEL, I
    ROBINSON, JB
    [J]. CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1977, 55 (24): : 4180 - 4183
  • [4] NEW CHIRAL BUILDING-BLOCKS AND THEIR APPLICATION TO THE CONSTRUCTION OF CHIRAL AMINOALCOHOLS - ENANTIOMERICALLY PURE CIS-3-MESYLOXY-4-HYDROXY AND TRANS-3-MESYLOXY-4-HYDROXY TETRAHYDROFURANS
    BORNER, A
    HOLZ, J
    KAGAN, HB
    [J]. TETRAHEDRON LETTERS, 1993, 34 (33) : 5273 - 5276
  • [5] Application of indane-derived C-2-symmetric bis(oxazolines) in two-point binding asymmetric Diels-Alder reactions
    Davies, IW
    Senanayake, CH
    Larsen, RD
    Verhoeven, TR
    Reider, PJ
    [J]. TETRAHEDRON LETTERS, 1996, 37 (11) : 1725 - 1726
  • [6] CHEMOENZYMATIC SYNTHESIS OF 1,2-AMINO-ALCOHOLS AND 1,3-AMINO-ALCOHOLS AND THEIR USE IN THE ENANTIOSELECTIVE REDUCTION OF ACETOPHENONE AND ANTI-ACETOPHENONE OXIME METHYL-ETHER WITH BORANE
    DIDIER, E
    LOUBINOUX, B
    TOMBO, GMR
    RIHS, G
    [J]. TETRAHEDRON, 1991, 47 (27) : 4941 - 4958
  • [7] FISCHER, 1995, J ORG CHEM, V60, P2026
  • [8] RING-CHAIN TAUTOMERISM IN OXAZOLIDINES
    FULOP, F
    PIHLAJA, K
    NEUVONEN, K
    BERNATH, G
    ARGAY, G
    KALMAN, A
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (07) : 1967 - 1969
  • [9] THE BIOSYNTHESIS OF SPERMIDINE .3. THE STEREOCHEMISTRY OF THE FORMATION OF THE N-CH2 GROUP IN THE BIOSYNTHESIS OF SPERMIDINE
    GOLDING, BT
    NASSEREDDIN, IK
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1985, (10): : 2017 - 2024
  • [10] On the mechanism of asymmetric nucleophilic ring-opening of epoxides catalyzed by (salen)Cr-III complexes
    Hansen, KB
    Leighton, JL
    Jacobsen, EN
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (44) : 10924 - 10925