Nucleophilic allylation-heterocyclization via bis-π-allylpalladium complexes:: Synthesis of five- and six-membered heterocycles

被引：12

作者：

Bao, M ^{[1
]}

Nakamura, H ^{[1
]}

Inoue, A ^{[1
]}

Yamamoto, Y ^{[1
]}

机构：

[1] Tohoku Univ, Grad Sch Sci, Dept Chem, Sendai, Miyagi 9808578, Japan

来源：

CHEMISTRY LETTERS | 2002年 / 02期

关键词：

D O I：

10.1246/cl.2002.158

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The reaction of the allylic halides 5-9 having an aldehyde or an imine moiety in the molecule with allyltributylstannane proceeded smoothly in the presence of Pd-2.dba(3)-CHCl3 (5 mol%) in DMF or THF, giving the corresponding heterocycles 10-14 in good to high yields. The Stille coupling product was not obtained under these reaction conditions.

引用

页码：158 / 159

页数：2

共 17 条

[1] Synthesis of (+/-)-10-epi-elemol by a highly stereoselective intramolecular palladium-catalyzed coupling of an allylstannane with an allyl acetate
Cuerva, JM
GomezBengoa, E
Mendez, M
Echavarren, AM
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (22) : 7540 - 7541
[2] Farina V., 1997, ORG REACT, V50, P1, DOI DOI 10.1002/0471264180.or050.01
[3] FARINA V, 1996, ADV MET ORG, V5, P1
[4] CATALYZED CROSS-COUPLING OF ALLYL BROMIDES WITH ALLYL TIN REAGENTS
GODSCHALX, J
STILLE, JK
[J]. TETRAHEDRON LETTERS, 1980, 21 (27) : 2599 - 2602
[5] CARBON CARBON BOND FORMATION BY INDUCED ELIMINATION FROM UNSYMMETRICALLY SUBSTITUTED (ALLYL)(ALLYL') PALLADIUM COMPLEXES
GOLIASZEWSKI, A
SCHWARTZ, J
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1984, 106 (17) : 5028 - 5030
[6] INTERCEPTION OF BIS(ETA-3-ALLYLIC)PALLADIUM INTERMEDIATES BY MALEIC-ANHYDRIDE - A CHANGE IN AN OVERALL CARBON CARBON BOND FORMING SCHEME USING ORGANOTIN REAGENTS
GOLIASZEWSKI, A
SCHWARTZ, J
[J]. ORGANOMETALLICS, 1985, 4 (02) : 417 - 419
[7] MITCHELL TN, 1992, SYNTHESIS-STUTTGART, P803
[8] Nakamura H, 2001, ANGEW CHEM INT EDIT, V40, P3208, DOI 10.1002/1521-3773(20010903)40:17<3208::AID-ANIE3208>3.0.CO
[9] 2-U
[10] Catalytic amphiphilic allylation via bis-π-allylpalladium complexes and its application to the synthesis of medium-sized carbocycles
Nakamura, H
Aoyagi, K
Shim, JG
Yamamoto, Y
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (03) : 372 - 377

← 1 2 →