ENANTIOSELECTIVE SYNTHESIS OF TROPANES BY REACTION OF RHODIUM-STABILIZED VINYLCARBENOIDS WITH PYRROLES

被引：35

作者：

DAVIES, HML

HUBY, NJS

机构：

[1] Department of Chemistry, Wake Forest University, Winston-Salem, NC 27109

来源：

TETRAHEDRON LETTERS | 1992年 / 33卷 / 46期

关键词：

D O I：

10.1016/S0040-4039(00)60899-7

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Rhodium(II) catalyzed decomposition of vinyldiazomethanes containing either (R)-pantolactone or (S)-lactate as chiral auxiliary in the presence of N-(tert-butoxycarbonyl)pyrrole resulted in an enantioselective entry to tropanes by a tandem cyclopropanation/Cope rearrangement.

引用

页码：6935 / 6938

页数：4

共 25 条

[1] N-MODIFIED ANALOGS OF COCAINE - SYNTHESIS AND INHIBITION OF BINDING TO THE COCAINE RECEPTOR
ABRAHAM, P
PITNER, JB
LEWIN, AH
BOJA, JW
KUHAR, MJ
CARROLL, FI
[J]. JOURNAL OF MEDICINAL CHEMISTRY, 1992, 35 (01) : 141 - 144
[2] ASYMMETRIC-SYNTHESIS OF PERMETHRIC ACID - STEREOCHEMISTRY OF CHIRAL COPPER CARBENOID REACTION
ARATANI, T
YONEYOSHI, Y
NAGASE, T
[J]. TETRAHEDRON LETTERS, 1982, 23 (06) : 685 - 688
[3] SYNTHESIS OF NOR-ANATOXIN-A AND ANATOXIN-A
CAMPBELL, HF
EDWARDS, OE
KOLT, R
[J]. CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1977, 55 (08): : 1372 - 1379
[4] COCAINE RECEPTOR - BIOCHEMICAL-CHARACTERIZATION AND STRUCTURE-ACTIVITY-RELATIONSHIPS OF COCAINE ANALOGS AT THE DOPAMINE TRANSPORTER
CARROLL, FI
LEWIN, AH
BOJA, JW
KUHAR, MJ
[J]. JOURNAL OF MEDICINAL CHEMISTRY, 1992, 35 (06) : 969 - 981
[5] COMPOUNDS AFFECTING CENTRAL NERVOUS-SYSTEM .4. 3BETA-PHENYLTROPANE-2-CARBOXYLIC ESTERS AND ANALOGS
CLARKE, RL
DAUM, SJ
GAMBINO, AJ
ACETO, MD
PEARL, J
LEVITT, M
CUMISKEY, WR
BOGADO, EF
[J]. JOURNAL OF MEDICINAL CHEMISTRY, 1973, 16 (11) : 1260 - 1267
[6] CONVENIENT SYNTHESIS OF VINYLDIAZOMETHANES FROM ALPHA-DIAZO-BETA-KETO ESTERS AND RELATED SYSTEMS
DAVIES, HML
HOUGLAND, PW
CANTRELL, WR
[J]. SYNTHETIC COMMUNICATIONS, 1992, 22 (07) : 971 - 978
[7] SYNTHESIS OF (+/-)-FERRUGININE AND (+/-)-ANHYDROECGONINE METHYL-ESTER BY A TANDEM CYCLOPROPANATION COPE REARRANGEMENT
DAVIES, HML
SAIKALI, E
YOUNG, WB
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (19) : 5696 - 5700
[8] ALPHA-HYDROXY ESTERS AS INEXPENSIVE CHIRAL AUXILIARIES IN RHODIUM(II)-CATALYZED CYCLOPROPANATIONS WITH VINYLDIAZOMETHANES
DAVIES, HML
CANTRELL, WR
[J]. TETRAHEDRON LETTERS, 1991, 32 (45) : 6509 - 6512
[9] HIGH ENANTIOSELECTIVITY IN THE INTRAMOLECULAR CYCLOPROPANATION OF ALLYL DIAZOACETATES USING A NOVEL RHODIUM(II) CATALYST
DOYLE, MP
PIETERS, RJ
MARTIN, SF
AUSTIN, RE
OALMANN, CJ
MULLER, P
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (04) : 1423 - 1424
[10] DOYLE MP, 1991, RECL TRAV CHIM PAY B, V110, P305

← 1 2 3 →