STEREOSELECTIVE CONVERGENT SYNTHESIS OF HYDROAZULENES VIA AN INTERMOLECULAR CYCLOPROPANATION COPE REARRANGEMENT

被引：34
作者：
CANTRELL, WR [1 ]
DAVIES, HML [1 ]
机构：
[1] WAKE FOREST UNIV,DEPT CHEM,WINSTON SALEM,NC 27109
来源：
JOURNAL OF ORGANIC CHEMISTRY | 1991年 / 56卷 / 02期
关键词：
D O I：
10.1021/jo00002a044
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Rhodium(II) acetate catalyzed decomposition of vinyldiazomethane 1 to a vinylcarbenoid intermediate in the presence of oxygenated dienes led to the direct formation of hydroazulenes 7, 13, and 15-19. The 3 + 4 annulation proceeds by a tandem cyclopropanation/Cope rearrangement sequence. The cyclopropanation is highly stereoselective, favoring the formation of cis-divinylcyclopropanes. Due to the boat transition state required for the Cope rearrangement of cis-divinylcyclopropanes, the hydroazulenes are formed with predictable stereocontrol.
引用
收藏
页码：723 / 727
页数：5
相关论文
共 37 条
[1]   DIAZOTRANSFER REACTIONS WITH PARA-ACETAMIDOBENZENESULFONYL AZIDE [J].
BAUM, JS ;
SHOOK, DA ;
DAVIES, HML ;
SMITH, HD .
SYNTHETIC COMMUNICATIONS, 1987, 17 (14) :1709-1716
[2]  
DANISHEFSKY S, 1983, ORG SYNTH, V61, P147
[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]   NOVEL-APPROACH TO 7-MEMBERED RINGS BY THE INTRAMOLECULAR TANDEM CYCLOPROPANATION COPE REARRANGEMENT SEQUENCE [J].
DAVIES, HML ;
OLDENBURG, CEM ;
MCAFEE, MJ ;
NORDAHL, JG ;
HENRETTA, JP ;
ROMINES, KR .
TETRAHEDRON LETTERS, 1988, 29 (09) :975-978
[6]   SCOPE AND STEREOCHEMISTRY OF THE TANDEM INTRAMOLECULAR CYCLOPROPANATION COPE REARRANGEMENT SEQUENCE [J].
DAVIES, HML ;
MCAFEE, MJ ;
OLDENBURG, CEM .
JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (04) :930-936
[7]   MECHANISTIC ASPECTS OF FORMAL [3 + 4] CYCLOADDITIONS BETWEEN VINYLCARBENOIDS AND FURANS [J].
DAVIES, HML ;
CLARK, DM ;
ALLIGOOD, DB ;
EIBAND, GR .
TETRAHEDRON, 1987, 43 (19) :4265-4270
[8]   [3 + 4] CYCLO-ADDITION REACTIONS OF VINYL CARBENOIDS WITH FURANS [J].
DAVIES, HML ;
CLARK, DM ;
SMITH, TK .
TETRAHEDRON LETTERS, 1985, 26 (46) :5659-5662
[9]  
DAVIES HML, 1989, ETRAHEDRON LETT, V30, P5057
[10]   REGIOSELECTIVITY IN CATALYTIC CYCLOPROPANATION REACTIONS [J].
DOYLE, MP ;
DOROW, RL ;
TAMBLYN, WH ;
BUHRO, WE .
TETRAHEDRON LETTERS, 1982, 23 (22) :2261-2264
1234