ENANTIOSELECTIVE SYNTHESIS OF DELTACYCLENES USING A [COI2ZN] CATALYTIC-SYSTEM

被引：39

作者：

PARDIGON, O ^{[1
]}

BUONO, G ^{[1
]}

机构：

[1] UNIV AIX MARSEILLE III,FAC SCI & TECH ST JEROME,ENSSPICAM,URA 1410,AVE ESCADRILLE NIEMEN,F-13397 MARSEILLE 20,FRANCE

来源：

TETRAHEDRON-ASYMMETRY | 1993年 / 4卷 / 09期

关键词：

D O I：

10.1016/S0957-4166(00)82243-0

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The efficient chiral catalyst [CoI2:Zn/(L*)n] readily promotes the homo Diels-Alder reactions between norbornadiene 1 and alkynes 2, affording tetracyclic compounds called ''deltatcyclenes'' 3. In this [2+2+2] cycloadditions, stereochemical control is achieved through the presence of catalytic amount of homochiral mono and bidentate ligands leading to deltacyclenes in high chemical and optical yields.

引用

收藏

页码：1977 / 1980

页数：4

相关论文

共 13 条

[1] 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

[2] 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

[3]

BRUNNER H, 1990, ANGEW CHEM, V102, P680

[4]

CROS P, 1987, NEW J CHEM, V11, P573

[5] ALPHA-METHOXY-ALPHA-TRIFLUOROMETHYLPHENYLACETIC ACID, A VERSATILE REAGENT FOR DETERMINATION OF ENANTIOMERIC COMPOSITION OF ALCOHOLS AND AMINES [J].

DALE, JA ;

DULL, DL ;

MOSHER, HS .

JOURNAL OF ORGANIC CHEMISTRY, 1969, 34 (09) :2543-&

[6] NUCLEAR MAGNETIC-RESONANCE ENANTIOMER REAGENTS - CONFIGURATIONAL CORRELATIONS VIA NUCLEAR MAGNETIC-RESONANCE CHEMICAL-SHIFTS OF DIASTEREOMERIC MANDELATE, O-METHYLMANDELATE, AND ALPHA-METHOXY-ALPHA-TRIFLUOROMETHYLPHENYLACETATE (MTPA) ESTERS [J].

DALE, JA ;

MOSHER, HS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1973, 95 (02) :512-519

[7]

DUAN IF, 1991, J CHEM SOC CHEM COMM, V95, P1347

[8] ACYCLIC STEREOSELECTION .42. 1,4-STEREOSELECTION AND 1,5-STEREOSELECTION BY SEQUENTIAL ALDOL ADDITION TO ALPHA,BETA-UNSATURATED ALDEHYDES FOLLOWED BY CLAISEN REARRANGEMENT - APPLICATION TO TOTAL SYNTHESIS OF THE VITAMIN-E SIDE-CHAIN AND THE ARCHAEBACTERIAL-C40 DIOL [J].

HEATHCOCK, CH ;

FINKELSTEIN, BL ;

JARVI, ET ;

RADEL, PA ;

HADLEY, CR .

JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (09) :1922-1942

[9]

HEUMANN A, 1993, J ORG CHEM, V57, P1276

[10] SCOPE OF THE COBALT-CATALYZED [2+2+2] HOMO-DIELS-ALDER REACTION [J].

LAUTENS, M ;

CRUDDEN, CM .

ORGANOMETALLICS, 1989, 8 (11) :2733-2735