Stereoselective Synthesis of Nipecotic Acid Derivatives via Palladium-Catalyzed Decarboxylative Cyclization of γ-Methylidene-δ-valerolactones with Imines

被引：41

作者：

Shintani, Ryo ^{[1
]}

Murakami, Masataka ^{[1
]}

Hayashi, Tamio ^{[1
]}

机构：

[1] Kyoto Univ, Grad Sch Sci, Dept Chem, Sakyo Ku, Kyoto 6068502, Japan

来源：

ORGANIC LETTERS | 2009年 / 11卷 / 02期

关键词：

PIPERIDINES; CYCLOADDITION; HYDROGENATION; INTERMEDIATE; ALKYLATION; ALLYLATION; GENERATION; KETONES;

D O I：

10.1021/ol802569q

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new synthetic method of multisubstituted nipecotic acid (piperidine-3-carboxylic acid) derivatives has been developed by way of palladium-catalyzed decarboxylative cyclization of gamma-methylidene-delta-valerolactones with imines. By employing the diethoxyphosphinoyl group as the N-protecting group for imines, the reaction proceeds smoothly with high diastereoselectivity. The products thus obtained can be further derivatized with high efficiency under simple reaction conditions.

引用

页码：457 / 459

页数：3

共 27 条

[1] Asymmetric allylic alkylation of ketone enolates: An asymmetric claisen surrogate [J].

Burger, EC ;

Tunge, JA .

ORGANIC LETTERS, 2004, 6 (22) :4113-4115

[2]

Clausen RP, 2006, ADV PHARMACOL, V54, P265, DOI 10.1016/S1054-3589(06)54011-6

[3] Proline-mediated enantioselective construction of tetrahydropyridines via a cascade Mannich-Type/Intramolecular Cyclization reaction [J].

Han, Rong-Gang ;

Wang, Yao ;

Li, Yu-Ye ;

Xu, Peng-Fei .

ADVANCED SYNTHESIS & CATALYSIS, 2008, 350 (10) :1474-1478

[4] Asymmetric hydrogenation of pyridines: Enantioselective synthesis of nipecotic acid derivatives [J].

Lei, Aiwen ;

Chen, Mao ;

He, Minsheng ;

Zhang, Xumu .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2006, 2006 (19) :4343-4347

[5] Design, synthesis and activity of ascorbic acid prodrugs of nipecotic, kynurenic and diclophenamic acids, liable to increase neurotropic activity [J].

Manfredini, S ;

Pavan, B ;

Vertuani, S ;

Scaglianti, M ;

Compagnone, D ;

Biondi, C ;

Scatturin, A ;

Tanganelli, S ;

Ferraro, L ;

Prasad, P ;

Dalpiaz, A .

JOURNAL OF MEDICINAL CHEMISTRY, 2002, 45 (03) :559-562

[6] Deracemization of quaternary stereocenters by Pd-catalyzed enantioconvergent decarboxylative allylation of racemic β-ketoesters [J].

Mohr, JT ;

Behenna, DC ;

Harned, AM ;

Stoltz, BM .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (42) :6924-6927

[7] Synthesis and GABA uptake inhibitory properties of 6-aryl iminoxymethyl substituted nipecotic acids [J].

N'Goka, V ;

Stenbol, TB ;

Krogspard-Larsen, P ;

Schlewer, G .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2004, 39 (10) :889-895

[8] Palladium-catalyzed decarboxylative aza-Michael addition-allylation reactions between allyl carbamates and activated olefins. Generation of quaternary carbon adjacent to secondary amine carbon center [J].

Patil, Nitin T. ;

Huo, Zhibao ;

Yamamoto, Yoshinori .

JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (18) :6991-6995

[9] Catalytic decarboxylative Sp-Sp3 coupling [J].

Rayabarapu, DK ;

Tunge, JA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (39) :13510-13511

[10] [4+2] cycloadditions of N-alkenyl iminium ions:: Structurally complex heterocycles from a three-component Diels-Alder reaction sequence [J].

Sarkar, Nihar ;

Banerjee, Abhisek ;

Nelson, Scott G. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (29) :9222-+

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