Vanadium-catalyzed asymmetric cyanohydrin synthesis

被引:150
作者
Belokon, YN
North, M [1 ]
Parsons, T
机构
[1] Kings Coll London, Dept Chem, London WC2R 2LS, England
[2] Russian Acad Sci, Inst Organoelement Cpds, Moscow 117813, Russia
关键词
D O I
10.1021/ol005893e
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHICS] Based on a mechanistic understanding of asymmetric cyanohydrin synthesis catalyzed by chiral titanium-salen complexes, a new catalyst based on vanadlum(IV) has been developed. The chiral (salen)VO catalyst is more enantioselective than the titanium based systems, 0.1 mol % of the catalyst being sufficient to convert aromatic and aliphatic aldehydes into the corresponding trimethylsilyl ethers of cyanohydrins with 68-95% enantiomeric excess at room temperature.
引用
收藏
页码:1617 / 1619
页数:3
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共 22 条
  • [1] Asymmetric trimethylsilylcyanation of aldehydes catalyzed by chiral (salen)Ti(IV) complexes.
    Belokon, Y
    Ikonnikov, N
    Moscalenko, M
    North, M
    Orlova, S
    Tararov, V
    Yashkina, L
    [J]. TETRAHEDRON-ASYMMETRY, 1996, 7 (03) : 851 - 855
  • [2] Asymmetric trimethylsilylcyanation of benzaldehyde catalyzed by (salen)Ti(IV) complexes derived from (R)- and/or (S)-4-hydroxy-5-formyl[2.2]paracyclophane and diamines
    Belokon, Y
    Moscalenko, M
    Ikonnikov, N
    Yashkina, L
    Antonov, D
    Vorontsov, E
    Rozenberg, V
    [J]. TETRAHEDRON-ASYMMETRY, 1997, 8 (19) : 3245 - 3250
  • [3] Asymmetric addition of trimethylsilyl cyanide to aldehydes catalysed by chiral (salen)Ti-IV complexes
    Belokon, Y
    Flego, M
    Ikonnikov, N
    Moscalenko, M
    North, M
    Orizu, C
    Tararov, V
    Tasinazzo, M
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1997, (09): : 1293 - 1295
  • [4] Asymmetric trimethylsilylcyanation of aldehydes catalyzed by chiral salen TiIV complexes with the C1 symmetry
    Belokon, YN
    Yashkina, LV
    Moscalenko, MA
    Chesnokov, AA
    Kublitsky, VS
    Ikonnikov, NS
    Orlova, SA
    Tararov, VI
    North, M
    [J]. RUSSIAN CHEMICAL BULLETIN, 1997, 46 (11) : 1936 - 1938
  • [5] Chiral salen-metal complexes as novel catalysts for asymmetric phase transfer alkylations
    Belokon, YN
    North, M
    Kublitski, VS
    Ikonnikov, NS
    Krasik, PE
    Maleev, VI
    [J]. TETRAHEDRON LETTERS, 1999, 40 (33) : 6105 - 6108
  • [6] The asymmetric addition of trimethylsilyl cyanide to aldehydes catalyzed by chiral (salen)titanium complexes
    Belokon, YN
    Caveda-Cepas, S
    Green, B
    Ikonnikov, NS
    Krustalev, VN
    Larichev, VS
    Moscalenko, MA
    North, M
    Orizu, C
    Tararov, VI
    Tasinazzo, M
    Timofeeva, GI
    Yashkina, LV
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (16) : 3968 - 3973
  • [7] BELOKON YN, IN PRESS EURO J ORG
  • [8] NOVEL REACTIVITY PATTERNS OF (N,N'-ETHYLENEBIS(SALICYLIDENEAMINATO))OXOVANADIUM(IV) IN STRONGLY ACIDIC MEDIA
    BONADIES, JA
    BUTLER, WM
    PECORARO, VL
    CARRANO, CJ
    [J]. INORGANIC CHEMISTRY, 1987, 26 (08) : 1218 - 1222
  • [9] EFFENBERGER F, 1994, ANGEW CHEM INT EDIT, V33, P1555, DOI 10.1002/anie.199415551
  • [10] Enantioselective addition of trimethylsilyl cyanide to aldehydes induced by a new chiral Ti(IV) complex
    Hwang, CD
    Hwang, DR
    Uang, BJ
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (20) : 6762 - 6763