A new aspect of magnesium bromide-promoted enantioselective aryl additions of triaryl(tetrahydrofuran)aluminum to ketones catalyzed by a titanium(IV) catalyst of trans-1,2-bis(hydroxycamphorsulfonylamino)cyclohexane

被引:29
作者
Chen, Chien-An [1 ]
Wu, Kuo-Hui [1 ]
Gau, Han-Mou [1 ]
机构
[1] Natl Chung Hsing Univ, Dept Chem, Taichung 402, Taiwan
关键词
asymmetric catalysis; disulfonamides; ketones; magnesium bromide; titanium; triarylaluminums;
D O I
10.1002/adsc.200800169
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
A novel aspect of MgBr2-promoted asymmetric triarylaluminum-tetrahydrofuran [AlAr3 (THF)] additions to ketones catalyzed by a titanium catalyst of 20 mol% trans-1,2-bis(hydroxycamphor-sulfonylamino)cyclohexane (2) is reported. The catalytic system works excellently for aromatic ketones with either an electron-withdrawing or an electron-donating substituent on the aromatic ring at the 2'-, 3'-, or 4'-positions, affording tertiary alcohols in excellent enantioselectivities of >= 90% ee, except for the cases of phenyl addition to 2'-methoxyacetophenone and 4-trimethylsilylphenyl (4-TMSC6H4) addition to acetopheneone.
引用
收藏
页码:1626 / 1634
页数:9
相关论文
共 76 条
  • [1] RETRACTED: Asymmetric Ni-catalyzed arylation of aromatic aldehydes with arylboroxines (Retracted Article)
    Arao, Takafumi
    Kondo, Kazuhiro
    Aoyama, Toyohiko
    [J]. TETRAHEDRON, 2007, 63 (24) : 5261 - 5264
  • [2] Insight into the mechanism of the asymmetric addition of alkyl groups to aldehydes catalyzed by titanium - BINOLate species
    Balsells, J
    Davis, TJ
    Carroll, P
    Walsh, PJ
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (35) : 10336 - 10348
  • [3] Development of the first practical catalyst for the asymmetric addition of alkyl- and arylzinc reagents to ketones
    Betancort, JM
    García, C
    Walsh, PJ
    [J]. SYNLETT, 2004, (05) : 749 - 760
  • [4] Remarkably stable (Me3Al)2•DABCO and stereoselective nickel-catalyzed AlR3 (R = Me, Et) additions to aldehydes
    Biswas, K
    Prieto, O
    Goldsmith, PJ
    Woodward, S
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (15) : 2232 - 2234
  • [5] Biswas K., 2005, ANGEW CHEM, V117, P2272
  • [6] Catalytic enantioselective aryl transfer:: asymmetric addition of diphenylzinc to aldehydes
    Bolm, C
    Muñiz, K
    [J]. CHEMICAL COMMUNICATIONS, 1999, (14) : 1295 - 1296
  • [7] Bolm C, 2001, ANGEW CHEM INT EDIT, V40, P1488, DOI 10.1002/1521-3773(20010417)40:8<1488::AID-ANIE1488>3.0.CO
  • [8] 2-B
  • [9] Bolm C, 2001, ANGEW CHEM INT EDIT, V40, P3285
  • [10] Bolm C, 2000, ANGEW CHEM INT EDIT, V39, P3465, DOI 10.1002/1521-3773(20001002)39:19<3465::AID-ANIE3465>3.0.CO