A palladium-catalyzed route to chiral 1,2,3-trisubstituted cyclopropanes

被引：0

作者：

Michelet, V ^{[1
]}

Genet, JP ^{[1
]}

机构：

[1] ECOLE NATL SUPER CHIM,ORGAN SYNTH LAB,CNRS,F-75231 PARIS 05,FRANCE

来源：

BULLETIN DE LA SOCIETE CHIMIQUE DE FRANCE | 1996年 / 133卷 / 09期

关键词：

alkylation; cyclopropanation; decarboalkoxylation; palladium(0) catalyst; chiral vinylic cyclopropane;

D O I：

暂无

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

An easy and efficient method for the synthesis of 1,2,3-trisubstituted vinylic cyclopropanes is described. The key steps are alkylation of chiral allylic alcohols, cyclization of functionalized allylic substates using a palladium(0) catalyst and decarboalkoxylation.

引用

页码：881 / 889

页数：9

共 44 条

[31] ENANTIOSELECTIVE, RHODIUM CATALYZED INTRAMOLECULAR CYCLOPROPANATIONS OF HOMOALLYTIC DIAZOACETATES [J].

MARTIN, SF ;

OALMANN, CJ ;

LIRAS, S .

TETRAHEDRON LETTERS, 1992, 33 (45) :6727-6730

[32] ENANTIOSELECTIVITY AND DIASTEREOSELECTIVITY IN THE INTRAMOLECULAR CYCLOPROPANATION OF SECONDARY ALLYLIC DIAZOACETATES [J].

MARTIN, SF ;

SPALLER, MR ;

LIRAS, S ;

HARTMANN, B .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (10) :4493-4494

[33]

MASAMUNE S, 1990, TETRAHEDRON LETT, V31, P6005

[34]

Michelet V, 1996, SYNLETT, P215

[35]

MICHELET V, 1995, SYNTHESIS-STUTTGART, P165

[36] ODORIFEROUS C11 HYDROCARBONS FROM HAWAIIAN DICTYOPTERIS [J].

MOORE, RE ;

PETTUS, JA ;

MISTYSYN, J .

JOURNAL OF ORGANIC CHEMISTRY, 1974, 39 (15) :2201-2207

[37] C2-SYMMETRICAL 4,4',5,5'-TETRAHYDROBI(OXAZOLES) AND 4,4',5,5'-TETRAHYDRO-2,2'-METHYLENEBIS[OXAZOLES] AS CHIRAL LIGANDS FOR ENANTIOSELECTIVE CATALYSIS [J].

MULLER, D ;

UMBRICHT, G ;

WEBER, B ;

PFALTZ, A .

HELVETICA CHIMICA ACTA, 1991, 74 (01) :232-240

[38] NEW CHIRAL RUTHENIUM BIS(OXAZOLINYL)PYRIDINE CATALYST - EFFICIENT ASYMMETRIC CYCLOPROPANATION OF OLEFINS WITH DIAZOACETATES [J].

NISHIYAMA, H ;

ITOH, Y ;

MATSUMOTO, H ;

PARK, SB ;

ITOH, K .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (05) :2223-2224

[39] CHIRAL METAL-COMPLEXES AS DISCRIMINATING MOLECULAR CATALYSTS [J].

NOYORI, R .

SCIENCE, 1990, 248 (4960) :1194-1199

[40] OPTICALLY-ACTIVE CYCLOPROPANES [J].

SALAUN, J .

CHEMICAL REVIEWS, 1989, 89 (05) :1247-1270

← 1 2 3 4 5 →