Influence of the temperature on the enantioselectivity of the cobalt catalysed homo Diels-Alder reactions

被引：23

作者：

Pardigon, O

Tenaglia, A

Buono, G

机构：

[1] Univ Aix Marseille, CNRS, UMR 6516, Ecole Natl Super Synth Proc & Ingn Chim, F-13397 Marseille 20, France

[2] Ctr Rech Ingn & Technol, F-69053 Decines Charpieu, France

来源：

JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL | 2003年 / 196卷 / 1-2期

关键词：

enantioselective; cobalt; cycloaddition; chiral P ligands; isoinversion principle;

D O I：

10.1016/S1381-1169(02)00646-5

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：

Depending on the variation of the temperature and on the nature of the substituent of alk-1-ynes 2, the enantioselectivity of the deltacyclene formation in the cobalt catalysed [2 + 2 + 2] cycloaddition of norbornadiene 1 and acetylenes 2, can be achieved with up to 98%. The best enantioselectivities observed around WC are in agreement with the Isoinversion principle (lip). (C) 2002 Elsevier Science B.V. All rights reserved.

引用

收藏

页码：157 / 164

页数：8

相关论文

共 34 条

[1] TIME-DEPENDENT MEASUREMENTS AND MOLECULAR STRUCTURE - OZONE [J].

BERRY, RS .

REVIEWS OF MODERN PHYSICS, 1960, 32 (02) :447-454

[2] CORRELATION OF RATES OF INTRAMOLECULAR TUNNELING PROCESSES, WITH APPLICATION TO SOME GROUP-V COMPOUNDS [J].

BERRY, RS .

JOURNAL OF CHEMICAL PHYSICS, 1960, 32 (03) :933-938

[3] Homo-Diels-Alder reactions of 2,4,6-tri-tert-butyl-1,3,5-triphospha-Dewar-benzene [J].

Binger, P ;

Leininger, S ;

Regitz, M ;

Bergstrasser, U ;

Bruckmann, J ;

Kruger, C .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1997, 529 (1-2) :215-221

[4] THE TEMPERATURE-DEPENDENCE OF THE DIASTEREOSELECTIVE REDUCTION OF 2-T-BUTYLCYCLOHEXANONE WITH DIISOBUTYL-ALUMINUM-2,6-DI-T-BUTYL-4-METHYLPHENOXIDE [J].

BRUNNE, J ;

HOFFMANN, N ;

SCHARF, HD .

TETRAHEDRON, 1994, 50 (23) :6819-6824

[5]

Brunner H, 1997, B SOC CHIM FR, V134, P307

[6] ASYMMETRICAL CATALYSIS .70. HIGHLY ENANTIOSELECTIVE COBALT-CATALYZED HOMO DIELS-ALDER REACTION OF NORBORNADIENE WITH ACETYLENES [J].

BRUNNER, H ;

PRESTER, F .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1991, 414 (03) :401-409

[7] ASYMMETRIC CATALYSTS .55. OPTICALLY-ACTIVE DELTACYCLANES AND DELTACYCLENES BY ENANTIOSELECTIVE CATALYSIS [J].

BRUNNER, H ;

MUSCHIOL, M ;

PRESTER, F .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1990, 29 (06) :652-653

[8] THE ISOINVERSION PRINCIPLE - A GENERAL-MODEL OF CHEMICAL SELECTIVITY [J].

BUSCHMANN, H ;

SCHARF, HD ;

HOFFMANN, N ;

ESSER, P .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1991, 30 (05) :477-515

[9] Diastereoselective addition of n-butyllithium to 2-phenylpropanal: A reassessment of the solvent and temperature effects [J].

Cainelli, G ;

Giacomini, D ;

Galletti, P ;

Marini, A .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1996, 35 (23-24) :2849-2852

[10] Opening norbornadiene homo Diels-Alder adducts to bicyclic systems [J].

Chen, Y ;

Snyder, JK .

TETRAHEDRON LETTERS, 1997, 38 (09) :1477-1480

← 1 2 3 4 →