THIOL AND DISULFIDE DERIVATIVES OF EPHEDRA ALKALOIDS .2. A MECHANISTIC STUDY OF THEIR EFFECT ON THE ADDITION OF DIETHYL ZINC TO BENZALDEHYDE

被引：79

作者：

FITZPATRICK, K ^{[1
]}

HULST, R ^{[1
]}

KELLOGG, RM ^{[1
]}

机构：

[1] UNIV GRONINGEN,GRONINGEN CTR CATALYSIS & SYNTH,DEPT ORGAN & MOLEC INORGAN CHEM,9747 AG GRONINGEN,NETHERLANDS

来源：

TETRAHEDRON-ASYMMETRY | 1995年 / 6卷 / 08期

关键词：

D O I：

10.1016/0957-4166(95)00237-J

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Thiol and disulfide derivatives of ephedrine have been shown previously to catalyse in high enantiomeric excess (ee) the reaction of diethyl zinc with benzaldehyde. We find that this reaction involves non-linear correlations between the ee of product and catalyst. Osmotic measurements indicate a high degree of aggregation of the zinc thiolates. The behaviour of the thiol derivatives deviates sharply from that of the oxygen analogue, N-methyl ephedrine.

引用

页码：1861 / 1864

页数：4

共 11 条

[1] ENANTIOSELECTIVE ADDITION OF DIETHYLZINC TO BENZALDEHYDE IN THE PRESENCE OF EPHEDRINE DERIVATIVES
CHALONER, PA
PERERA, SAR
[J]. TETRAHEDRON LETTERS, 1987, 28 (26) : 3013 - 3014
[2] NONLINEAR EFFECTS IN ASYMMETRIC CATALYSIS
GUILLANEUX, D
ZHAO, SH
SAMUEL, O
RAINFORD, D
KAGAN, HB
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (21) : 9430 - 9439
[3] SULFUR DERIVATIVES OF EPHEDRA ALKALOIDS - NEW AND HIGHLY EFFICIENT CHIRAL CATALYSTS
HOF, RP
POELERT, MA
PEPER, NCMW
KELLOGG, RM
[J]. TETRAHEDRON-ASYMMETRY, 1994, 5 (01) : 31 - 34
[4] ENANTIOSELECTIVE ADDITION OF DIETHYLZINC TO ALPHA-BRANCHED ALDEHYDES
KANG, J
LEE, JW
KIM, JI
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1994, (17) : 2009 - 2010
[5] SELF AND NONSELF RECOGNITION OF ASYMMETRIC CATALYSTS - NONLINEAR EFFECTS IN THE AMINO ALCOHOL-PROMOTED ENANTIOSELECTIVE ADDITION OF DIALKYLZINCS TO ALDEHYDES
KITAMURA, M
SUGA, S
NIWA, M
NOYORI, R
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (17) : 4832 - 4842
[6] ENANTIOSELECTIVE ADDITION OF DIALKYLZINCS TO ALDEHYDES PROMOTED BY CHIRAL AMINO-ALCOHOLS - MECHANISM AND NONLINEAR EFFECT
KITAMURA, M
OKADA, S
SUGA, S
NOYORI, R
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (11) : 4028 - 4036
[7] ENANTIOSELECTIVE ADDITION OF ORGANOMETALLIC REAGENTS TO CARBONYL-COMPOUNDS - CHIRALITY TRANSFER, MULTIPLICATION, AND AMPLIFICATION
NOYORI, R
KITAMURA, M
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1991, 30 (01) : 49 - 69
[8] POELERT MA, 1994, HETEROCYCLES, V37, P461
[9] NONLINEAR EFFECTS IN ASYMMETRIC-SYNTHESIS - EXAMPLES IN ASYMMETRIC OXIDATIONS AND ALDOLIZATION REACTIONS
PUCHOT, C
SAMUEL, O
DUNACH, E
ZHAO, S
AGAMI, C
KAGAN, HB
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (09) : 2353 - 2357
[10] CHIRAL N,N-DIALKYLNOREPHEDRINES AS CATALYSTS OF THE HIGHLY ENANTIOSELECTIVE ADDITION OF DIALKYLZINCS TO ALIPHATIC AND AROMATIC-ALDEHYDES - THE ASYMMETRIC-SYNTHESIS OF SECONDARY ALIPHATIC AND AROMATIC ALCOHOLS OF HIGH OPTICAL PURITY
SOAI, K
YOKOYAMA, S
HAYASAKA, T
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (13) : 4264 - 4268

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