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

[31] Poly(phosphonate)-mediated Horner-Wadsworth-Emmons reactions
Steinbach, Tobias
Wahlen, Christian
Wurm, Frederik R.
POLYMER CHEMISTRY, 2015, 6 (07) : 1192 - 1202
[32] ASYMMETRIC CARBOALKOXYALKYLIDENATION WITH A CHIRAL HORNER-WADSWORTH-EMMONS REAGENT
DENMARK, SE
RIVERA, I
JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (23): : 6887 - 6889
[33] Lewis Base Activation of Silyl Acetals: Iridium-Catalyzed Reductive Horner-Wadsworth-Emmons Olefination
Dakarapu, Udaya Sree
Bokka, Apparao
Asgari, Parham
Trog, Gabriela
Hua, Yuanda
Nguyen, Hiep H.
Rahman, Nawal
Jeon, Junha
ORGANIC LETTERS, 2015, 17 (23) : 5792 - 5795
[34] IMPROVED HORNER-WADSWORTH-EMMONS OLEFINATION OF BASE SENSITIVE GAMMA-CHIRAL BETA-KETOPHOSPHONATES
KOSKINEN, AMP
KOSKINEN, PM
SYNLETT, 1993, (07) : 501 - 502
[35] Synthetic applications of asymmetric Horner-Wadsworth-Emmons condensations: Approaches to marine natural products
Tullis, JS
Helquist, P
Rein, T
PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 1999, 144 : 165 - 168
[36] Application of Horner-Wadsworth-Emmons olefination for the synthesis of granulatamide A, its E isomer and other amides of tryptamine
Pakhare, Deepali
Kusurkar, Radhika
NEW JOURNAL OF CHEMISTRY, 2016, 40 (06) : 5428 - 5431
[37] New and efficient conditions for the Z-selective synthesis of unsaturated esters by the Horner-Wadsworth-Emmons olefination
Touchard, FP
TETRAHEDRON LETTERS, 2004, 45 (28) : 5519 - 5523
[38] Synthesis of a [14C]-steroid intermediate: an application of a nonstabilized Horner-Wadsworth-Emmons olefination approach
Rivera, Nelo R.
Ren, Sumei
Hesk, David
JOURNAL OF LABELLED COMPOUNDS & RADIOPHARMACEUTICALS, 2015, 58 (01): : 20 - 22
[39] Efficient and scalable protocol for the Z-selective synthesis of unsaturated esters by Horner-Wadsworth-Emmons olefination
Touchard, FP
Capelle, N
Mercier, M
ADVANCED SYNTHESIS & CATALYSIS, 2005, 347 (05) : 707 - 711
[40] Mixed 1,1-Bisphosphorus Compounds: Synthesis, Alkylation, and Horner-Wadsworth-Emmons Olefination Reactions
Ortial, Stephanie
Thompson, Dane A.
Montchamp, Jean-Luc
JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (23): : 8166 - 8179

← 1 2 3 4 5 →