Palladium catalysed reactions of allene with active methylene pronucleophiles.: C-1,3-dienylmethyl derivatives and their Diels-Alder reactions

被引：20

作者：

Grigg, R ^{[1
]}

Kongathip, N

Kongathip, B

Luangkamin, S

Dondas, HA

机构：

[1] Univ Leeds, Sch Chem, MIDAS, Leeds LS2 9JT, W Yorkshire, England

[2] Kasetsart Univ, Sci & Arts Fac, Dept Chem, Bangkok, Thailand

[3] Mersin Univ, Sci & Arts Fac, Dept Chem, Mersin, Turkey

来源：

TETRAHEDRON | 2001年 / 57卷 / 44期

关键词：

atom economy; pi-allylpalladium (II) species; allene dimerisation; chromans; bis-allylation;

D O I：

10.1016/S0040-4020(01)00924-3

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A 2-step 100% atom economic sequence is reported whereby active methylene pronucleophiles react with 2 mol equiv. of allene to give bis-1,3-dienylmethyl derivatives of the pronucleophiles. Subsequent double Diels-Alder reactions furnish 1,1'-linked cyclohexenes with a 3-carbon spacer. (C) 2001 Published by Elsevier Science Ltd.

引用

页码：9187 / 9197

页数：11

共 20 条

[1] PALLADIUM-CATALYZED ADDITION OF MALONATE TYPE COMPOUNDS TO ALLENES VIA A HYDROPALLADATION PROCESS
BESSON, L
GORE, J
GAZES, B
[J]. TETRAHEDRON LETTERS, 1995, 36 (22) : 3853 - 3856
[2] BROENE RD, 1995, COMPREHENSIVE ORGANO, V12, P323
[3] BETA-MIGRATORY INSERTION REACTIONS OF (ETA-5-C5R'5)RH(L)(C2H4)R+BF4- (R' = H, CH3 R = H, C2H5 L = P(OME)3, PME3) - COMPARISON OF THE ENERGETICS OF HYDRIDE VERSUS ALKYL MIGRATION
BROOKHART, M
HAUPTMAN, E
LINCOLN, DM
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (26) : 10394 - 10401
[4] Palladium catalysed queuing processes. Part 1: Termolecular cyclization-anion capture employing carbon monoxide as a relay switch and hydride, organotin(IV) or boron reagents
Brown, S
Clarkson, S
Grigg, R
Thomas, WA
Sridharan, V
Wilson, DM
[J]. TETRAHEDRON, 2001, 57 (07) : 1347 - 1359
[5] TRANSITION-METAL CATALYZED REACTIONS OF ALLENE
COULSON, DR
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1973, 38 (08) : 1483 - 1490
[6] GOULD ES, 1959, MECHANISM STRUCTURE, P379
[7] Palladium catalysed reaction of allene with phenols. Phenoxymethyl-1,3-dienes and their further reactions
Grigg, R
Kongkathip, N
Kongkathip, B
Luangkamin, S
Dondas, HA
[J]. TETRAHEDRON, 2001, 57 (37) : 7965 - 7978
[8] Palladium catalysed reactions of allenes, carbon monoxide and nucleophiles.
Grigg, R
Monteith, M
Sridharan, V
Terrier, C
[J]. TETRAHEDRON, 1998, 54 (15) : 3885 - 3894
[9] Mechanistic aspects of asymmetric hydroformylation of olefins catalyzed by chiral phosphine-phosphite-rhodium(I) complexes
Horiuchi, T
Shirakawa, E
Nozaki, K
Takaya, H
[J]. ORGANOMETALLICS, 1997, 16 (13) : 2981 - 2986
[10] Palladium-catalyzed carbocyclization/silastannylation and distannylation of bis(allenes)
Kang, SK
Baik, TG
Kulak, AN
Ha, YH
Lim, Y
Park, J
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (46) : 11529 - 11530

← 1 2 →