Stereoselective three-component cascade synthesis of α-substituted 2,4-dienamides from gem-difluorochloro ethanes

被引：5

作者：

Das, Shyamsundar ^{[1
]}

Ko, Nakeun ^{[2
]}

Lee, Eunsung ^{[2
]}

Kim, Sang Eun ^{[1
,3
,4
]}

Lee, Byung Chul ^{[1
,3
]}

机构：

[1] Seoul Natl Univ, Bundang Hosp, Coll Med, Dept Nucl Med, Seongnam 13620, South Korea

[2] Pohang Univ Sci & Technol, Dept Chem, Pohang 37673, South Korea

[3] Adv Inst Convergence Technol, Ctr Nanomol Imaging & Innovat Drug Dev, Suwon 16229, South Korea

[4] Seoul Natl Univ, Grad Sch Convergence Sci & Technol, Dept Transdisciplinary Studies, Seoul 08826, South Korea

来源：

CHEMICAL COMMUNICATIONS | 2019年 / 55卷 / 95期

基金：

新加坡国家研究基金会;

关键词：

ELECTRON-DEFICIENT ALKENES; WILLIAMSON ETHER SYNTHESIS; REARRANGEMENT; DERIVATIVES; CYCLOADDITIONS; CYCLIZATION; SEQUENCE; KETONES; ACCESS; POTENT;

D O I：

10.1039/c9cc07100h

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Herein, we describe a new transition metal-free Claisen rearrangement for the synthesis of alpha-substituted 2,4-dienamides. The one-pot, stereoselective three-component cascade reaction between a series of propargyl alcohols, amines, and gem-difluorochloro ethane derivatives afforded various polysubstituted 2,4-dienamides in good yields. This synthetic method for 1,1-captodative dienes, alpha-substituted 2,4-dienamides, can be utilized for preparing pharmaceutical analogues containing an indolin-2-one or lactone moiety.

引用

页码：14355 / 14358

页数：4

共 47 条

[1] Friedel-Crafts reaction of activated benzene rings with captodative and electron-deficient alkenes. A one-step synthesis of the natural product methyl 3-(2,4,5-trimethoxyphenyl)propionate [J].

Aguilar, R ;

Benavides, A ;

Tamariz, J .

SYNTHETIC COMMUNICATIONS, 2004, 34 (15) :2719-2735

[2] REACTION OF COPPER ENOLATES OF ESTERS WITH PROPARGYLIC SYSTEMS - FACILE PREPARATION OF 3,4-DIENOIC ESTERS, STEREOSELECTIVE REARRANGEMENT TO (2E,4Z)-DIENOIC AND (2E,4E)-DIENOIC ESTERS, AND STEREOSELECTIVE SYNTHESIS OF A FRAGRANCE FROM BARTLETT PEAR [J].

AMOS, RA ;

KATZENELLENBOGEN, JA .

JOURNAL OF ORGANIC CHEMISTRY, 1978, 43 (04) :555-560

[3] Superbase promoted synthesis of dienamides as useful intermediates for the synthesis of α-ketoamides, γ-lactams and cyclic imino ethers [J].

Blangetti, Marco ;

Deagostino, Annamaria ;

Gervasio, Giuliana ;

Marabello, Domenica ;

Prandi, Cristina ;

Venturello, Paolo .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2011, 9 (07) :2535-2538

[4]

BROWN CA, 1993, ORG SYNTH, V8, P553

[5] Sequential reactions promoted by manganese:: Completely stereoselective synthesis of (E)-α,β-unsaturated amides, ketones, aldehydes, and carboxylic acids [J].

Concellon, Jose M. ;

Rodriguez-Solla, Humberto ;

Diaz, Pamela .

JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (21) :7974-7979

[6] Metal-mediated alkynediol cycloisomerization: first and second generation formal total syntheses of didemniserinolipid B [J].

Das, Shyamsundar ;

Induvadana, Boddeti ;

Ramana, C. V. .

TETRAHEDRON, 2013, 69 (07) :1881-1896

[7] Brook/Elimination/Aldol Reaction (BEAR) Sequence for the Direct Preparation of Fluorinated Aldols from β,β-Difluoro-α-(trimethylsilyl)alcohols [J].

Decostanzi, Melanie ;

Van Der Lee, Arie ;

Campagne, Jean-Marc ;

Leclerc, Eric .

ADVANCED SYNTHESIS & CATALYSIS, 2015, 357 (14-15) :3091-3097

[8] Ynamides: Versatile Tools in Organic Synthesis [J].

Evano, Gwilherm ;

Coste, Alexis ;

Jouvin, Kevin .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (16) :2840-2859

[9] A mild and efficient asymmetric hetero-Diels-Alder reaction of the Brassard diene with aldehydes [J].

Fan, Q ;

Lin, LL ;

Liu, J ;

Huang, YZ ;

Feng, XM .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2005, 2005 (16) :3542-3552

[10] Selective inhibition of osteoclast vacuolar H+-ATPase [J].

Farina, C ;

Gagliardi, S .

CURRENT PHARMACEUTICAL DESIGN, 2002, 8 (23) :2033-2048

← 1 2 3 4 5 →