Chiral 8-substituted 2-(2-methoxyphenyl) and 2-(2-hydroxyphenyl)-5,6,7,8-tetrahydro-6,6-dimethyl-5,7-methanoquinolines as ligands for enantioselective catalysis: palladium catalyzed allylic substitution and addition of diethylzinc to benzaldehyde

被引：13

作者：

Chelucci, G ^{[1
]}

Craba, S ^{[1
]}

Saba, A ^{[1
]}

Soccolini, F ^{[1
]}

Sotgiu, G ^{[1
]}

机构：

[1] Univ Sassari, Dipartimento Chim, I-07100 Sassari, Italy

来源：

JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL | 2000年 / 164卷 / 1-2期

关键词：

chiral tetrahydroquinolines; palladium complex; allylic substitution; addition of diethylzinc; enantioselectivity;

D O I：

10.1016/S1381-1169(00)00373-3

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：

Diastereomeric pure 8-substituted 2-(2-methoxyphenyl) and 2-(2-hydroxyphenyl)-5,6,7,8-tetrahydro-6,6-dimethyl-5,7-methanoquinolines were prepared and assessed in the enantioselective palladium catalyzed allylic substitution of 1,3-diphenylprop-Zenyl acetate with dimethyl malonate and addition of diethylzinc to benzaldehyde. Enantioselectivity up to 61% was obtained. (C) 2000 Elsevier Science B.V. All rights reserved.

引用

页码：173 / 179

页数：7

共 9 条

[1] Chiral 8-amino substituted 2-phenyl-5,6,7,8-tetrahydro-6,6-dimethyl- @ methanoquinolines as chiral ligands for enantioselective catalysis: palladium catalysed allylic substitution and addition of diethylzinc to benzaldehyde
Tetrahedron: Asymmetry, 8 (15):
[2] Chiral 8-amino substituted 2-phenyl-5,6,7,8-tetrahydro-6,6-dimethylmethanoquinolines as chiral ligands for enantioselective catalysis: Palladium catalysed allylic substitution and addition of diethylzinc to benzaldehyde
Chelucci, G
Pinna, GA
Saba, A
TETRAHEDRON-ASYMMETRY, 1997, 8 (15) : 2571 - 2578
[3] Synthesis of new chiral catalysts, substituted 2-phenyl-5,6,7,8-tetrahydro-6,6-dimethyl-5,7-methano-quinolines, for the enantioselective addition of diethylzinc to benzaldehyde
Collomb, P
vonZelewsky, A
TETRAHEDRON-ASYMMETRY, 1995, 6 (12) : 2903 - 2904
[4] Synthesis of new chiral catalysts, substituted 2-phenyl-5,6,7,8-tetrahydro-6,6-dimethyl- @5,7- methano-quinolines, for the enantioselective addition of diethylzinc to benzaldehyde
Tetrahedron Asymmetry, 12 (2903):
[5] A new synthesis method and crystal structure of 2-phenyl-5,6,7,8-tetrahydro-6,6-dimethyl-5,7-methano-8-quinolinol
Gao Yong-Guang
Mu Chu-Chun
Li Xin-Sheng
Xu Dong-Cheng
Su Hong
Wen Yi-Hang
CHINESE JOURNAL OF STRUCTURAL CHEMISTRY, 2008, 27 (06) : 663 - 666
[6] A New Synthesis Method and Crystal Structure of 2-Phenyl-5,6,7,8-tetrahydro-6,6-dimethyl-5,7-methano-8-quinolinol
高永光
牧初春
李新生
徐东成
苏虹
温一航
Chinese Journal of Structural Chemistry, 2008, (06) : 663 - 666
[7] A New Synthesis Method and Crystal Structure of 2-Phenyl-5,6,7,8-tetrahydro-6,6-dimethyl-5,7-methano-8-quinolinol
高永光
牧初春
李新生
徐东成
苏虹
温一航
结构化学, 2008, (06) : 663 - 666
[8] Chiral 2-(2-phenylthiophenyl)-5,6,7,8-tetrahydroquinolines: new N-S ligands for asymmetric catalysis - Palladium-catalyzed allylic alkylation and copper-catalyzed cyclopropanation reactions
Chelucci, G
Muroni, D
Pinna, GA
Saba, A
Vignola, D
JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2003, 191 (01) : 1 - 8
[9] Chiral 8-substituted 10,10-dimethyl-5-pyridin-2-yl-6-aza-tricyclo [7.1.1.02,7]undeca-2(7),3,5-trien-8-ols as enantioselective catalysts in the addition of diethylzinc to substituted benzaldehydes
Lin, RX
Chen, CP
JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2006, 243 (01) : 89 - 98

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