Et3B-promoted, Pd(0)-catalyzed allylation of active methylene compounds with allylic alcohols

被引：72

作者：

Tamaru, Y ^{[1
]}

Horino, Y ^{[1
]}

Araki, M ^{[1
]}

Tanaka, S ^{[1
]}

Kimura, M ^{[1
]}

机构：

[1] Nagasaki Univ, Fac Engn, Dept Appl Chem, Nagasaki 8528521, Japan

来源：

TETRAHEDRON LETTERS | 2000年 / 41卷 / 30期

关键词：

alcohols; allylation; boron and compounds; palladium and compounds;

D O I：

10.1016/S0040-4039(00)00934-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Triethylborane promotes the Pd(0)-catalyzed allylation of active methylene compounds (Meldrum's acid and malonates) with a variety of allylic alcohols. The reaction proceeds smoothly at room temperature and provides the allylation products in good yield. (C) 2000 Elsevier Science Ltd. All rights reserved.

引用

页码：5705 / 5709

页数：5

共 15 条

[1]

ATKINS KE, 1970, TETRAHEDRON LETT, P3821

[2] ALKYLATION OF ACTIVE METHYLENE-COMPOUNDS BY ALLYLIC ALCOHOLS USING TETRAKIS(TRIPHENYLPHOSPHINE)PALLADIUM(0) CATALYSTS [J].

BERGBREITER, DE ;

WEATHERFORD, DA .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1989, (13) :883-884

[3] STEREOSELECTIVE CONVERSION OF KETO GROUPS INTO METHYL VINYL QUATERNARY CARBON CENTERS [J].

BUCKWALTER, BL ;

BURFITT, IR ;

FELKIN, H ;

JOLYGOUDKET, M ;

NAEMURA, K ;

SALOMON, MF ;

WENKERT, E ;

WOVKULICH, PM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1978, 100 (20) :6445-6450

[4] ASYMMETRIC NICKEL-CATALYZED CROSS-COUPLING REACTION OF ALLYLIC SUBSTRATES WITH GRIGNARD-REAGENTS [J].

CONSIGLIO, G ;

PICCOLO, O ;

RONCETTI, L ;

MORANDINI, F .

TETRAHEDRON, 1986, 42 (07) :2043-2053

[5]

Godleslcy S., 1991, COMPREHENSIVE ORGANI, V4, P585

[6] SYNTHESIS OF ALPHA-AMINO-ACIDS BY ALKYLATION OF DIETHYL ACETAMIDOMALONATE IN THE PRESENCE OF PALLADIUM COMPLEXES [J].

HAUDEGOND, JP ;

CHAUVIN, Y ;

COMMEREUC, D .

JOURNAL OF ORGANIC CHEMISTRY, 1979, 44 (17) :3063-3065

[7] PALLADIUM AND ARSENIC(III) OXIDE-CATALYZED ALLYLIC ALKYLATION BY ALLYLIC ALCOHOLS UNDER NEUTRAL CONDITIONS [J].

LU, XY ;

LU, L ;

SUN, JH .

JOURNAL OF MOLECULAR CATALYSIS, 1987, 41 (1-2) :245-251

[8] PALLADIUM-CATALYZED ALLYLIC ALKYLATION OF CARBONUCLEOPHILES WITH ALLYLIC BORATES OR ALLYLIC ALCOHOLS AND BORON-OXIDE UNDER NEUTRAL CONDITIONS [J].

LU, XY ;

JIANG, XH ;

TAO, XC .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1988, 344 (01) :109-118

[9] Activation of C-O and C-N bonds in allylic alcohols and amines by palladium complexes promoted by CO2. Synthetic applications to allylation of nucleophiles, carbonylation, and allylamine disproportionation [J].

Sakamoto, M ;

Shimizu, I ;

Yamamoto, A .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1996, 69 (04) :1065-1078

[10] ALLYLIC ALCOHOLS AS SUBSTRATES FOR THE PALLADIUM(0)-CATALYZED ALLYLIC SUBSTITUTION [J].

STARY, I ;

STARA, IG ;

KOCOVSKY, P .

TETRAHEDRON LETTERS, 1993, 34 (01) :179-182

← 1 2 →