Pressure-dependent enantio selectivity in the organozinc addition to aldehydes in supercritical fluids

被引:16
作者
Jessop, PG [1 ]
Brown, RA
Yamakawa, M
Xiao, JL
Ikariya, T
Kitamura, M
Tucker, SC
Noyori, R
机构
[1] Univ Calif Davis, Dept Chem, Davis, CA 95616 USA
[2] Kinjo Gakuin Univ, Nagoya, Aichi 4638521, Japan
[3] Univ Liverpool, Dept Chem, Leverhulme Ctr Innovat Catalysis, Liverpool L69 7ZD, Merseyside, England
[4] Tokyo Inst Technol, Dept Chem Technol, Meguro Ku, Tokyo 1528552, Japan
[5] Nagoya Univ, Dept Chem, Nagoya, Aichi 4648602, Japan
基金
美国国家科学基金会;
关键词
alkylation; enantioselectivity; ethane; fluoroform; homogeneous catalysis; pressure effect; solvent effect;
D O I
10.1016/S0896-8446(02)00030-X
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
Amino alcohol-catalyzed asymmetric alkylation of benzaldehydes by dialkylzines can be achieved in supercritical fluoroform (scCH(3)) and supercritical ethane (SCC2H6) with high conversion and enantio selectivity. The higher enantioselectivity in ethane compared to CHF3 suggests that solvent polarity affects the reaction. The enantioselectivity in scCHF(3) is strongly pressure dependent. (C) 2002 Elsevier Science B.V. All rights reserved.
引用
收藏
页码:161 / 172
页数:12
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共 65 条
[61]   SOLVENT-DENSITY DEPENDENCE OF THE UNIMOLECULAR REACTION-RATE - DISSOCIATION REACTION OF 2-METHYL-2-NITROSOPROPANE DIMER IN CARBON-DIOXIDE FROM GAS TO LIQUID STATES [J].
YOSHIMURA, Y ;
KIMURA, Y .
CHEMICAL PHYSICS LETTERS, 1991, 181 (06) :517-520
[62]   THERMO-PHYSICAL PROPERTIES OF FLUIDS .2. METHANE, ETHANE, PROPANE, ISOBUTANE, AND NORMAL BUTANE [J].
YOUNGLOVE, BA ;
ELY, JF .
JOURNAL OF PHYSICAL AND CHEMICAL REFERENCE DATA, 1987, 16 (04) :577-798
[63]   STEADY-STATE AND TIME-RESOLVED FLUORESCENCE INVESTIGATIONS OF PYRENE EXCIMER FORMATION IN SUPERCRITICAL CO2 [J].
ZAGROBELNY, J ;
BETTS, TA ;
BRIGHT, FV .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (13) :5249-5257
[64]   INFLUENCE OF SOLUTE FLUID CLUSTERING ON THE PHOTOPHYSICS OF PYRENE EMISSION IN SUPERCRITICAL C2H4 AND CF3H [J].
ZAGROBELNY, J ;
BRIGHT, FV .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (20) :7821-7826
[65]   PROBING SOLUTE-ENTRAINER INTERACTIONS IN MATRIX-MODIFIED SUPERCRITICAL CO2 [J].
ZAGROBELNY, J ;
BRIGHT, FV .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (02) :701-707