Regioselective ring opening of vinylcyclopropanes by hydrogenation with palladium on activated carbon

被引:45
作者
Barrett, AGM
Tam, W
机构
[1] Department of Chemistry, Imp. Coll. Sci., Technol. and Med., London
关键词
D O I
10.1021/jo970879+
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A highly regioselective reductive ring opening of vinylcyclopropanes induced by palladium on activated carbon has been investigated. High yields and excellent regioselectivities were observed in cleaving either the less hindered bond or the more hindered bond of the cyclopropane depending on whether the substituent on the vinylcyclopropane is capable of coordinating to Pd or not.
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页码:7673 / 7678
页数:6
相关论文
共 43 条
[1]   STEREOCHEMISTRY OF PALLADIUM(II)-INDUCED RING-OPENING OF THE CYCLOPROPANE IN A VINYLCYCLOPROPANE - CHLOROPALLADATION OF CAR-2-ENE [J].
AHMAD, MU ;
BACKVALL, JE ;
NORDBERG, RE ;
NORIN, T ;
STROMBERG, S .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1982, (05) :321-323
[2]  
BACKVALL JE, 1985, J AM CHEM SOC, V107, P7408
[3]   STEREOCHEMISTRY OF CHLOROPALLADATION OF A VINYLCYCLOPROPANE - X-RAY CRYSTAL-STRUCTURE OF PD2CL2(C10H16CL)2 [J].
BACKVALL, JE ;
BJORKMAN, EE .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1982, (12) :693-694
[4]   Total synthesis and stereochemical assignment of the quinquecyclopropane-containing cholesteryl ester transfer protein inhibitor U-106305 [J].
Barrett, AGM ;
Hamprecht, D ;
White, AJP ;
Williams, DJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (33) :7863-7864
[5]   Total synthesis of the pentacyclopropane antifungal agent FR-900848 [J].
Barrett, AGM ;
Kasdorf, K .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (45) :11030-11037
[6]   Total synthesis of the antifungal agent FR-900848 [J].
Barrett, AGM ;
Kasdorf, K .
CHEMICAL COMMUNICATIONS, 1996, (03) :325-326
[7]  
BARRETT AGM, 1997, IN PRESS J ORG CHEM
[8]   THEORETICAL-STUDY OF THE CYCLOPROPANE RING-OPENING BY PALLADIUM(II) COMPLEXES [J].
BLOMBERG, MRA ;
SIEGBAHN, PEM ;
BACKVALL, JE .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (15) :4450-4456
[9]   DESIGN OF AMPHOTERIC BIFUNCTIONAL LIGANDS - APPLICATION TO THE ENANTIOSELECTIVE SIMMONS-SMITH CYCLOPROPANATION OF ALLYLIC ALCOHOLS [J].
CHARETTE, AB ;
JUTEAU, H .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (06) :2651-2652
[10]   SYNTHESIS OF ALTERNATING HYDROXY-SUBSTITUTED AND METHYL-SUBSTITUTED HYDROCARBONS BY OXYMERCURATION OF CYCLOPROPYLCARBINOLS [J].
COLLUM, DB ;
STILL, WC ;
MOHAMADI, F .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (08) :2094-2096