ANOMALOUS REACTIVITY OF MONO SUBSTITUTED RHODIUM STABILIZED VINYLCARBENOIDS

被引:61
作者
DAVIES, HML
SAIKALI, E
CLARK, TJ
CHEE, EH
机构
[1] Department of Chemistry, Wake Forest University, Winston-Salem, NC 27109
关键词
D O I
10.1016/S0040-4039(00)97047-3
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
In contrast to rhodium(lI) stabilized vinylcarbenoids with two electron withdrawing groups, the related mono substituted vinylcarbenoids exhibit reactivity at either the carbenoid center or the vinylogous position. The site of reactivity may be controlled by appropriate catalysts and solvents, leading to the effective synthesis of bicyclic systems by a tandem cyclopropanation/Cope rearrangement sequence. © 1990.
引用
收藏
页码:6299 / 6302
页数:4
相关论文
共 22 条
[1]   CYCLIZATION OF 3-DIAZOALKENES TO PYRAZOLES [J].
BREWBAKER, JL ;
HART, H .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1969, 91 (03) :711-+
[2]   AN IMPROVED METHOD FOR THE SYNTHESIS OF ALPHA-DIAZO KETONES [J].
DANHEISER, RL ;
MILLER, RF ;
BRISBOIS, RG ;
PARK, SZ .
JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (06) :1959-1964
[3]   TANDEM CYCLOPROPANATION COPE REARRANGEMENT SEQUENCE - STEREOSPECIFIC [3 + 4] CYCLOADDITION REACTION OF VINYLCARBENOIDS WITH CYCLOPENTADIENE [J].
DAVIES, HML ;
SMITH, HD ;
KORKOR, O .
TETRAHEDRON LETTERS, 1987, 28 (17) :1853-1856
[4]   NOVEL ENTRY TO THE TROPANE SYSTEM BY REACTION OF RHODIUM(II) ACETATE STABILIZED VINYLCARBENOIDS WITH PYRROLES [J].
DAVIES, HML ;
YOUNG, WB ;
SMITH, HD .
TETRAHEDRON LETTERS, 1989, 30 (35) :4653-4656
[5]   [3 + 4] CYCLO-ADDITION REACTIONS OF VINYL CARBENOIDS WITH FURANS [J].
DAVIES, HML ;
CLARK, DM ;
SMITH, TK .
TETRAHEDRON LETTERS, 1985, 26 (46) :5659-5662
[6]  
DAVIES HML, 1987, TETRAHEDRON, V17, P4265
[7]   CATALYTIC METHODS FOR METAL CARBENE TRANSFORMATIONS [J].
DOYLE, MP .
CHEMICAL REVIEWS, 1986, 86 (05) :919-939
[8]  
DVIES HML, 1989, J ORG CHEM, V54, P930
[9]   THE ASYMMETRIC-SYNTHESIS OF ALPHA-AMINO-ACIDS - ELECTROPHILIC AZIDATION OF CHIRAL IMIDE ENOLATES, A PRACTICAL APPROACH TO THE SYNTHESIS OF (R)-ALPHA-AZIDO AND (S)-ALPHA-AZIDO CARBOXYLIC-ACIDS [J].
EVANS, DA ;
BRITTON, TC ;
ELLMAN, JA ;
DOROW, RL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (10) :4011-4030
[10]   FISCHER CARBENE MEDIATED CONVERSIONS OF ENYNES TO BICYCLIC AND TRICYCLIC CYCLOPROPANE-CONTAINING CARBON SKELETONS [J].
KORKOWSKI, PF ;
HOYE, TR ;
RYDBERG, DB .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (08) :2676-2678