Mild conditions for the synthesis of functionalized pyrrolidines via Pd-catalyzed carboamination reactions

被引：46

作者：

Bertrand, Myra Beaudoin ^{[1
]}

Leathen, Matthew L. ^{[1
]}

Wolfe, John P. ^{[1
]}

机构：

[1] Univ Michigan, Dept Chem, Ann Arbor, MI 48109 USA

来源：

ORGANIC LETTERS | 2007年 / 9卷 / 03期

关键词：

D O I：

10.1021/ol062808f

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The palladium-catalyzed carboamination of N-protected gamma-aminoalkenes with aryl bromides and triflates has been achieved under new, mild reaction conditions using the weak base Cs2CO3 in dioxane solvent. These reactions tolerate a wide variety of functional groups, including enolizable ketones, nitro groups, methyl esters, and acetates, which are not compatible with previously described conditions.

引用

页码：457 / 460

页数：4

共 22 条

[1] Identification of the effective palladium(0) catalytic species generated in situ from mixtures of Pd(dba)(2) and bidentate phosphine ligands. Determination of their rates and mechanism in oxidative addition
Amatore, C
Broeker, G
Jutand, A
Khalil, F
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (22) : 5176 - 5185
[2] Synthesis and biological activity of pyrrole, pyrroline and pyrrolidine derivatives with two aryl groups on adjacent positions
Bellina, Fabio
Rossi, Renzo
[J]. TETRAHEDRON, 2006, 62 (31) : 7213 - 7256
[3] Stereoselective synthesis of N-protected pyrrolidines via Pd-catalyzed reactions of γ-(N-acylamino) alkenes and γ-(N-Boc-amino) alkenes with aryl bromides
Bertrand, MB
Wolfe, JP
[J]. TETRAHEDRON, 2005, 61 (26) : 6447 - 6459
[4] A concise stereoselective synthesis of Preussin, 3-epi-Preussin, and analogues
Bertrand, Myra Beaudoin
Wolfe, John P.
[J]. ORGANIC LETTERS, 2006, 8 (11) : 2353 - 2356
[5] Intramolecular dipolar cycloaddition reactions of azomethine ylides
Coldham, I
Hufton, R
[J]. CHEMICAL REVIEWS, 2005, 105 (07) : 2765 - 2809
[6] Palladium(II)-catalyzed intramolecular aminocarbonylation of endo-carbamates under Wacker-type conditions
Harayama, H
Abe, A
Sakado, T
Kimura, M
Fugami, K
Tanaka, S
Tamaru, Y
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (07) : 2113 - 2122
[7] HARTWIG JF, 2002, MODERN ARENE CHEM, P107
[8] A flexible approach to (S)-5-alkyl tetramic acid derivatives:: Application to the asymmetric synthesis of (+)-preussin and protected (3S,4S)-AHPPA
Huang, PQ
Wu, TJ
Ruan, YP
[J]. ORGANIC LETTERS, 2003, 5 (23) : 4341 - 4344
[9] Kadota I, 1997, HETEROCYCLES, V46, P335
[10] SYNTHESIS OF PYRROLIDINES AND PIPERIDINES VIA PALLADIUM-CATALYZED COUPLING OF VINYLIC HALIDES AND OLEFINIC SULFONAMIDES
LAROCK, RC
YANG, H
WEINREB, SM
HERR, RJ
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (15) : 4172 - 4178

← 1 2 3 →