Route to α-Aryl Phosphonoacetates: Useful Synthetic Precursors in the Horner-Wadsworth-Emmons Olefination

被引：5

作者：

VanGelder, Kelsey F. ^{[1
]}

Wang, Melinda ^{[1
]}

Kozlowski, Marisa C. ^{[1
]}

机构：

[1] Univ Penn, Dept Chem, Roy & Diana Vagelos Labs, Philadelphia, PA 19104 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2015年 / 80卷 / 20期

基金：

美国国家科学基金会; 美国国家卫生研究院;

关键词：

FORMING REDUCTIVE ELIMINATION; STABILIZED CARBANIONS; ARYLATION; ANALOGS; INHIBITORS; COMPLEXES; DISCOVERY; LIGANDS; ESTERS; ACID;

D O I：

10.1021/acs.joc.5b01887

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A versatile and general catalytic strategy has been developed for the alpha-arylation of phosphonoacetates utilizing parallel microscale experimentation. These a-substituted phosphonoacetates are widely useful, notably as substrates in the Horner-Wadsworth-Emmons-type olefinations. However, the current routes to these products involve harsh conditions, limiting the variety of functionality. The reported method can be used with a variety of aryl chlorides and aryl bromides, including several heterocyclic examples.

引用

页码：10288 / 10293

页数：6

共 50 条

[41] Asymmetric Horner-Wadsworth-Emmons reactions with aldehyde substrates: Scope and synthetic applications.
Rein, T
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1997, 213 : 400 - ORGN
[42] Enantioselective preparation of allenecarboxylates by asymmetric Horner-Wadsworth-Emmons reaction
Tetrahedron Lett, 21 (3735):
[43] Computational study of the Horner-Wadsworth-Emmons reactions for their reactivity and selectivity
Sambasivarao, Somisetti
DuBay, Kateri
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2015, 250
[44] Preparation of α,β-Unsaturated Diazoketones Employing a Horner-Wadsworth-Emmons Reagent
Pinho, Vagner D.
Burtoloso, Antonio C. B.
JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (01): : 289 - 292
[45] A novel synthetic approach to glycerophospholipids via Horner-Wadsworth-Emmons reaction of mixed phosphonoacetate
Sano, Shigeki
Sumiyoshi, Hayato
Handa, Atsushi
Tokizane, Rie
Nakao, Michiyasu
TETRAHEDRON LETTERS, 2015, 56 (32) : 4686 - 4688
[46] Horner-Wadsworth-Emmons Reactions in THF: Effect of Hydroperoxide Species
Jarvis, Amanda G.
Wells, Elizabeth R.
Fairlamb, Ian J. S.
SYNLETT, 2013, 24 (12) : 1493 - 1496
[47] Enantioselective preparation of allenecarboxylates by asymmetric Horner-Wadsworth-Emmons reaction
Tanaka, K
Otsubo, K
Fuji, K
TETRAHEDRON LETTERS, 1996, 37 (21) : 3735 - 3738
[48] An olefin disconnection strategy for the practical synthesis of (+)-brefeldin A: olefin cross metathesis and intramolecular Horner-Wadsworth-Emmons olefination
Seo, Seung-Yong
Jung, Jae-Kyung
Paek, Seung-Mann
Lee, Yong-Sil
Kim, Seok-Ho
Suh, Young-Ger
TETRAHEDRON LETTERS, 2006, 47 (37) : 6527 - 6530
[49] Enantioselective synthesis of (+)-patulolide C via proline-catalyzed sequential α-aminooxylation and Horner-Wadsworth-Emmons olefination
Sabitha, Gowravaram
Chandrashekhar, G.
Yadagiri, K.
Yadav, J. S.
TETRAHEDRON LETTERS, 2010, 51 (29) : 3824 - 3826
[50] Strategy for the synthesis of 2,2-disubstituted 8-azachromanones via Horner-Wadsworth-Emmons olefination
Omelian, Taras V.
Ostapchuk, Eugeniy N.
Dobrydnev, Alexey V.
Malets, Yehor S.
Brovarets, Volodymyr S.
Grygorenko, Oleksandr O.
CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2020, 56 (02) : 213 - 218

← 1 2 3 4 5 →