QUANTUM-CHEMICAL MODELING OF CHIRAL CATALYSIS .14. ON THE COORDINATION OF CARBONYL-COMPOUNDS TO DIAZALUMINOLIDINE, OXAZALUMINOLIDINE AND DIOXALUMINOLIDINE OF POTENTIAL USE AS CHIRAL CONTROLLERS IN ORGANIC SYNTHETIC CHEMISTRY

被引:2
作者
NEVALAINEN, V
机构
[1] Division of Organic Chemistry, University of Helsinki, SF-00014
关键词
D O I
10.1016/S0957-4166(00)82232-6
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Conformers of 4-coordinate adducts of carbonyl compounds and diaza-, oxaza- and dioxaluminolidines were investigated by means of ab initio MO methods (RHF). Formaldehyde was used as a model of carbonyl compounds. Relative stabilities of the conformers indicate formation of syn adducts of carbonyl compounds and aluminolidines (C-c=o and aluminolidine ring syn about the Al-O-c=o bond) to be favoured over that of the corresponding anti ones (all synlanti ratios higher than 99:1, 6-31G//6-31G). The energetic preference for the formation of syn adducts of oxazaaluminolidines was about twice as high as that of diaza- or dioxaluminolidines of which the synlanti selectivities were found to be practically equal.
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页码:2517 / 2530
页数:14
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共 76 条
  • [1] CONTRIBUTIONS TO THE CHEMISTRY OF BORON .135. ADDITION-COMPOUNDS OF 1,3,2-DIAZABOROLIDINES WITH ALUMINUM AND GALLIUM HALIDES
    ANTON, K
    EURINGER, C
    NOTH, H
    [J]. CHEMISCHE BERICHTE-RECUEIL, 1984, 117 (03): : 1222 - 1234
  • [2] CATIONIC ALUMINUM HYDRIDES - [H2ALL]+[ALH4]-, L = N,N,N'N'',N''-PENTAMETHYLDIETHYLENETRIAMINE AND 1,4,8,11-TETRAMETHYL-1,4,8,11-TETRAAZACYCLOTETRADECANE
    ATWOOD, JL
    ROBINSON, KD
    JONES, C
    RASTON, CL
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1991, (23) : 1697 - 1699
  • [3] TERTIARY AMINE STABILIZED DIALANE
    ATWOOD, JL
    BENNETT, FR
    ELMS, FM
    JONES, C
    RASTON, CL
    ROBINSON, KD
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (21) : 8183 - 8185
  • [4] THEORETICAL INVESTIGATION OF ALUMINUM OXYGEN PI-BONDING IN 3-COORDINATE AND 4-COORDINATE ALUMINUM ALKOXIDES
    BARRON, AR
    DOBBS, KD
    FRANCL, MM
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (01) : 39 - 43
  • [5] PREPARATION AND PROPERTIES OF A NEUTRAL, CHELATED 4-COORDINATE ORGANOALUMINUM-NITROGEN DERIVATIVE
    BEACHLEY, OT
    RACETTE, KC
    [J]. INORGANIC CHEMISTRY, 1975, 14 (10) : 2534 - 2537
  • [6] CHELATION IN ORGANOALUMINUM-NITROGEN CHEMISTRY
    BEACHLEY, OT
    RACETTE, KC
    [J]. INORGANIC CHEMISTRY, 1976, 15 (09) : 2110 - 2115
  • [7] BENETT FR, 1992, ORGANOMETALLICS, V11, P1457
  • [8] BOMBI GG, 1990, INORG CHIM ACTA, V171, P79
  • [9] 7-COORDINATE ALUMINUM IN [ALCL2.BENZO-15-CROWN-5][ALCL3ET]
    BOTT, SG
    ELGAMAL, H
    ATWOOD, JL
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (06) : 1796 - 1797
  • [10] PI-COMPLEXES OF ALKENES TO TRIVALENT ALUMINUM
    CHEY, J
    CHOE, HS
    CHOOK, YM
    JENSEN, E
    SEIDA, PR
    FRANCL, MM
    [J]. ORGANOMETALLICS, 1990, 9 (09) : 2430 - 2436