A convenient synthesis of (E)-α-alkylidene-γ-lactams and (E)-3-alkylideneoxindoles by rhodium-catalyzed intramolecular hydroamidation

被引：39

作者：

Kobayashi, Y

Kamisaki, H

Yanada, K

Yanada, R

Takemoto, Y ^{[1
]}

机构：

[1] Kyoto Univ, Grad Sch Pharmaceut Sci, Sakyo Ku, Kyoto 6068501, Japan

[2] Setsunan Univ, Fac Pharmaceut Sci, Hirakata, Osaka 5730101, Japan

来源：

TETRAHEDRON LETTERS | 2005年 / 46卷 / 44期

关键词：

rhodium catalyst; carbonylative cyclization; C-H activation; formarnides; hydroamidation;

D O I：

10.1016/j.tetlet.2005.08.133

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Rhodium-catalyzed carbonylative cyclization without carbon monoxide was investigated. Cyclization of various form-amides having alkynyl groups proceeded smoothly in the presence of Rh-4(CO)(12) to provide alpha-alkylidene-gamma-lactams or 3-alkylideneoxindoles in moderate to good yields with high (E)-selectivity. (c) 2005 Elsevier Ltd. All rights reserved.

引用

收藏

页码：7549 / 7552

页数：4

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共 38 条

[21] A chemoselective and regioselective catalytic way to a novel nine-membered lactone [J].

Lenoble, G ;

Urrutigoïty, M ;

Kalck, P .

TETRAHEDRON LETTERS, 2001, 42 (22) :3697-3700

[22] Total synthesis of TMC-95A and -B via a new reaction leading to Z-enamides. Some preliminary findings as to SAR [J].

Lin, SN ;

Yang, ZQ ;

Kwok, BHB ;

Koldobskiy, M ;

Crews, CM ;

Danishefsky, SJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (20) :6347-6355

[23] PdCl2-catalyzed efficient transformation of propargylic amines to (E)-α-chloroalkylidene-β-lactams [J].

Ma, SM ;

Wu, B ;

Jiang, XF .

JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (07) :2588-2593

[24] Studies on Pd(II)-catalyzed synthesis of (Z)-α-haloalkylidene-β-lactones from cyclocarbonylation of 2-alkynols and the subsequent coupling reactions [J].

Ma, SM ;

Wu, B ;

Jiang, XF ;

Zhao, SM .

JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (07) :2568-2575

[25] Mild and efficient synthesis of (Z)-α-chloroalkylidene-β-lactones via the PdCl2-catalyzed cyclocarbonylation of 2-alkynols [J].

Ma, SM ;

Wu, B ;

Zhao, SM .

ORGANIC LETTERS, 2003, 5 (23) :4429-4432

[26] Evolution of carbonylation catalysis: No need for carbon monoxide [J].

Morimoto, T ;

Kakiuchi, K .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (42) :5580-5588

[27] Transition-metal-catalyzed reactions in heterocyclic synthesis [J].

Nakamura, I ;

Yamamoto, Y .

CHEMICAL REVIEWS, 2004, 104 (05) :2127-2198

[28] An efficient catalytic system for cyclocarbonylation of terpenes into lactones [J].

Nguyen, DH ;

Hebrard, F ;

Duran, J ;

Polo, A ;

Urrutigoíty, M ;

Kalck, P .

APPLIED ORGANOMETALLIC CHEMISTRY, 2005, 19 (01) :30-34

[29] Synthesis and stereochemistry of some bicyclic γ-lactones from parasitic wasps (Hymenoptera: Braconidae).: Utility of hydrolytic kinetic resolution of epoxides and palladium(II)-catalyzed hydroxycyclization-carbonylation-lactonization of ene-diols [J].

Paddon-Jones, GC ;

McErlean, CSP ;

Hayes, P ;

Moore, CJ ;

Konig, WA ;

Kitching, W .

JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (22) :7487-7495

[30] Cyclohydrocarbonylation of substituted alkynes and tandem cyclohydrocarbonylation-CO insertion of α-keto alkynes catalyzed by immobilized Co-Rh heterobimetallic nanoparticles [J].

Park, KH ;

Kim, SY ;

Chung, YK .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2005, 3 (03) :395-398

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