SYNTHESIS OF CHIRAL N-PROTECTED ALPHA-AMINO-BETA-DIKETONES FROM ALPHA-DIAZOKETONES DERIVED FROM NATURAL AMINO-ACIDS

被引:78
作者
YE, T [1 ]
MCKERVEY, MA [1 ]
机构
[1] QUEENS UNIV BELFAST,SCH CHEM,BELFAST BT9 5AG,ANTRIM,NORTH IRELAND
关键词
D O I
10.1016/S0040-4020(01)80473-7
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Alpha-Diazoketols, prepared by condensation of aldehydes or ketones with lithiated optically active alpha-diazoketones derived from natural amino acids, rearrange to homochiral alpha-amino-beat-diketones on treatment with rhodium(II) acetate.
引用
收藏
页码:8007 / 8022
页数:16
相关论文
共 22 条
  • [1] MEASUREMENT OF N-CARBETHOXYPROLINE AND N-CARBETHOXYGLYCINE IN MODEL SOLUTIONS AND IN WINE
    BAKER, JC
    OUGH, CS
    [J]. JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 1976, 24 (03) : 528 - 532
  • [2] ALPHA-AMINO-ACIDS AS CHIRAL EDUCTS FOR ASYMMETRIC PRODUCTS - AMINO ACYLATION WITH N-ACYLAMINO ACIDS
    BUCKLEY, TF
    RAPOPORT, H
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (20) : 6157 - 6163
  • [3] COLLINS J, 1990, THESIS NUI U COLLEGE
  • [4] AN IMPROVED METHOD FOR THE SYNTHESIS OF ALPHA-DIAZO KETONES
    DANHEISER, RL
    MILLER, RF
    BRISBOIS, RG
    PARK, SZ
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (06) : 1959 - 1964
  • [5] DAVIES JS, 1985, AMINO ACIDS PEPTIDES, P110
  • [6] DAVIES JS, 1985, AMINO ACIDS PEPTIDES, P98
  • [7] HIGH-PRESSURE APPROACH TO THE TOTAL SYNTHESIS OF 6-EPI-D-PURPUROSAMINE B
    GOLEBIOWSKI, A
    JACOBSSON, U
    JURCZAK, J
    [J]. TETRAHEDRON, 1987, 43 (13) : 3063 - 3066
  • [8] NAGAO K, 1983, SYNTHESIS-STUTTGART, P197
  • [9] Norlander J. E., 1984, J ORG CHEM, V49, P4107
  • [10] AN IMPROVED 2-STEP ROUTE FOR THE PREPARATION OF BETA-DIKETONES FROM ALDEHYDES AND ITS APPLICATION TO THE SYNTHESIS OF BETA-DAMASCONE
    PELLICCIARI, R
    FRINGUELLI, R
    SISANI, E
    CURINI, M
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1981, (09): : 2566 - 2569