Further developments in metal-catalysed C-C bond cleavage in allylic dimethyl malonate derivatives

被引：28

作者：

Bricout, H ^{[1
]}

Carpentier, JF ^{[1
]}

Mortreux, A ^{[1
]}

机构：

[1] ENSCL, CATALYSE HETEROGENE & HOMOGENE LAB, CNRS, GRP CHIM ORGAN APPL, F-59652 VILLENEUVE DASCQ, FRANCE

来源：

TETRAHEDRON LETTERS | 1997年 / 38卷 / 06期

关键词：

D O I：

10.1016/S0040-4039(96)02510-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The use of a catalytic amount of nickelbis(1,4-bis(diphenylphosphino)butane) in DMF enables the activation of the C-C bond in dimethyl allylmalonate derivatives to proceed under rather smooth reaction conditions, without added nucleophile. Several examples like isomerization of substituted-allyl malonate derivatives, racemization of chiral products, but also a synthetic application as an inverse disproportionation reaction are described. (C) 1997, Elsevier Science Ltd.

引用

页码：1053 / 1056

页数：4

共 16 条

[1] NICKEL-CATALYZED ALLYLATION OF STABLE ENOLATES BY ALLYLIC ETHERS AND ALLYLIC ALCOHOLS
ALVAREZ, E
CUVIGNY, T
JULIA, M
[J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1988, 339 (1-2) : 199 - 212
[2] Bis(aminophosphine)-nickel complexes as efficient catalysts for alkylation of allylic acetates with stabilized nucleophiles
Bricout, H
Carpentier, JF
Mortreux, A
[J]. TETRAHEDRON LETTERS, 1996, 37 (34) : 6105 - 6108
[3] NICKEL-CATALYZED SUBSTITUTION-REACTIONS OF ALLYLIC COMPOUNDS WITH SOFT NUCLEOPHILES - AN EFFICIENT ALTERNATIVE TO PALLADIUM CATALYSIS
BRICOUT, H
CARPENTIER, JF
MORTREUX, A
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1995, (18) : 1863 - 1864
[4] CHUIT C, 1968, J CHEM SOC CHEM COMM, P1604
[5] COLLMAN JP, 1987, PRINCIPLES APPLICATI
[6] STEREOCHEMICAL ASPECTS OF THE NICKEL-CATALYZED ALKYLATION OF ALLYLIC ALCOHOLS
CONSIGLIO, G
MORANDINI, F
PICCOLO, O
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (07) : 1846 - 1847
[7] ASYMMETRIC NICKEL-CATALYZED CROSS-COUPLING REACTION OF ALLYLIC SUBSTRATES WITH GRIGNARD-REAGENTS
CONSIGLIO, G
PICCOLO, O
RONCETTI, L
MORANDINI, F
[J]. TETRAHEDRON, 1986, 42 (07) : 2043 - 2053
[8] Heck R.F., 1985, PALLADIUM REAGENTS O
[9] NICKEL-CATALYZED SUBSTITUTION-REACTIONS OF ALLYLIC CARBONATES WITH ARYL-BORATES AND ALKENYL-BORATES
KOBAYASHI, Y
IKEDA, E
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1994, (15) : 1789 - 1790
[10] EXAMPLE OF THERMODYNAMIC CONTROL IN PALLADIUM-CATALYZED ALLYLIC ALKYLATION - EVIDENCE FOR PALLADIUM-ASSISTED ALLYLIC C-C BOND-CLEAVAGE
NILSSON, YIM
ANDERSSON, PG
BACKVALL, JE
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (15) : 6609 - 6613

← 1 2 →