Highly enantioselective conjugate addition of dialkylzinc reagents to acyclic nitroalkenes:: A catalytic route to β2-amino acids, aldehydes, and alcohols

被引:145
作者
Duursma, A [1 ]
Minnaard, AJ [1 ]
Feringa, BL [1 ]
机构
[1] Univ Groningen, Stratingh Inst, Dept Organ & Mol Inorgan Chem, NL-9747 AG Groningen, Netherlands
关键词
D O I
10.1021/ja029817d
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Using chiral phosphoramidite ligand (S,R,R)-L1 in the conjugate addition to acyclic nitroalkenes for the first time, we obtained enantioselectivities up to 98%. The use of acyclic substrates with different dialkylzinc reagents provides a catalytic enantioselective route to (functionalized) β2-amino aldehydes, acids, and alcohols. Copyright © 2003 American Chemical Society.
引用
收藏
页码:3700 / 3701
页数:2
相关论文
共 33 条
  • [1] Abele S, 2000, EUR J ORG CHEM, V2000, P1
  • [2] Alexakis A, 2001, SYNLETT, P1375
  • [3] Enantioselective copper-catalyzed conjugate addition of dialkyl zinc to nitro-olefins
    Alexakis, A
    Benhaim, C
    [J]. ORGANIC LETTERS, 2000, 2 (17) : 2579 - 2581
  • [4] Anada M, 2000, HETEROCYCLES, V52, P875
  • [5] Catalytic enantioselective synthesis of (-)-prostaglandin E1 methyl ester based on a tandem 1,4-addition-aldol reaction
    Arnold, LA
    Naasz, R
    Minnaard, AJ
    Feringa, BL
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (21) : 7244 - 7254
  • [6] ASEN S, 1959, J BIOL CHEM, V234, P343
  • [7] CONJUGATED NITROALKENES - VERSATILE INTERMEDIATES IN ORGANIC-SYNTHESIS
    BARRETT, AGM
    GRABOSKI, GG
    [J]. CHEMICAL REVIEWS, 1986, 86 (05) : 751 - 762
  • [8] TOTAL SYNTHESIS OF CRYPTOPHYCINS - REVISION OF THE STRUCTURES OF CRYPTOPHYCIN-A AND CRYPTOPHYCIN-C
    BARROW, RA
    HEMSCHEIDT, T
    LIANG, J
    PAIK, S
    MOORE, RE
    TIUS, MA
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (09) : 2479 - 2490
  • [9] Berner OM, 2002, EUR J ORG CHEM, V2002, P1877
  • [10] BROWN BR, 1994, ORGANIC CHEM ALIPHAT, P443