Highly enantioselective cyanosilylation of aldehydes catalyzed by novel β-amino alcohol-titanium complexes

被引:109
作者
Li, Y [1 ]
He, B [1 ]
Qin, B [1 ]
Feng, XM [1 ]
Zhang, GL [1 ]
机构
[1] Sichuan Univ, Coll Chem, Key Lab Green Chem & Technol, Minist Educ, Chengdu 610064, Peoples R China
关键词
D O I
10.1021/jo0488356
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The beta-amino alcohol 1b-Ti(Oi-Pr)(4) complex has been shown to catalyze the enantioselective cyanosilylation of aldehydes efficiently. In the presence of 5 mol % of lb-Ti(Oi-Pr)(4) complex catalyst, the aromatic, conjugated, heteroaromatic, and aliphatic aldehydes were converted to their corresponding trimethylsilyl ethers of cyanohydrins in 90-99% yields with up to 94% ee under mild conditions.
引用
收藏
页码:7910 / 7913
页数:4
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共 64 条
  • [1] BMPD, a novel C2-chiral 1,3-diketone ligand;: Synthesis and application to an asymmetric catalytic reaction
    Abiko, A
    Wang, GQ
    [J]. TETRAHEDRON, 1998, 54 (38) : 11405 - 11420
  • [2] A BMPD-yttrium isopropoxide complex: Highly efficient chiral Lewis acid catalyst for asymmetric silylcyanation
    Abiko, A
    Wang, GQ
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (07) : 2264 - 2265
  • [3] Catalytic, asymmetric cyanohydrin synthesis mediated by lanthanide(III) chloride pybox complexes
    Aspinall, HC
    Greeves, N
    Smith, PM
    [J]. TETRAHEDRON LETTERS, 1999, 40 (09) : 1763 - 1766
  • [4] 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
  • [5] 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
  • [6] 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
  • [7] Vanadium-catalyzed asymmetric cyanohydrin synthesis
    Belokon, YN
    North, M
    Parsons, T
    [J]. ORGANIC LETTERS, 2000, 2 (11) : 1617 - 1619
  • [8] Belokon YN, 2002, HELV CHIM ACTA, V85, P3301, DOI 10.1002/1522-2675(200210)85:10<3301::AID-HLCA3301>3.0.CO
  • [9] 2-2
  • [10] Catalytic asymmetric synthesis of O-acetyl cyanohydrins from KCN, Ac2O and aldehydes
    Belokon, YN
    Gutnov, AV
    Moskalenko, MA
    Yashkina, LV
    Lesovoy, DE
    Ikonnikov, NS
    Larichev, VS
    North, M
    [J]. CHEMICAL COMMUNICATIONS, 2002, (03) : 244 - 245