An efficient oxa-Michael addition to diethyl vinylphosphonate under mild reaction conditions

被引：12

作者：

Baszczynski, Ondrej ^{[1
]}

Jansa, Petr ^{[1
]}

Dracinsky, Martin ^{[1
]}

Kaiser, Martin Maxmilian ^{[1
]}

Spacek, Petr ^{[1
]}

Janeba, Zlatko ^{[1
]}

机构：

[1] Acad Sci Czech Republic, Inst Organ Chem & Biochem, Vvi, CR-16610 Prague 6, Czech Republic

来源：

RSC ADVANCES | 2012年 / 2卷 / 04期

关键词：

ACYCLIC NUCLEOSIDE PHOSPHONATES; HYPOXANTHINE-GUANINE PHOSPHORIBOSYLTRANSFERASE; DERIVATIVES; INHIBITION; RESISTANCE; ANALOGS; TARGET; WATER; ACIDS; DNA;

D O I：

10.1039/c2ra00938b

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

An oxa-Michael addition of various secondary and branched primary alcohols to diethyl vinylphosphonate was systematically studied and optimized. This efficient method precedes using of harsh reaction conditions (e.g. strong bases, high temperatures) and gains access to an important class of biologically active compounds in one step.

引用

页码：1282 / 1284

页数：3

共 50 条

[31] Synergistic zinc catalyst mediated oxa-Michael kinetic resolution reaction
Peng, Tianyu
Zhu, Haiyong
Xu, Yingfan
Li, Dan
Wang, Yuan
Wang, Linqing
Liu, Xin
Yang, Dongxu
Wang, Rui
ORGANIC CHEMISTRY FRONTIERS, 2021, 8 (13) : 3463 - 3468
[32] Oxa-Michael Addition to α,β-Unsaturated Nitriles: An Expedient Route to γ-Amino Alcohols and Derivatives
Guo, Beibei
Zijlstra, Douwe S.
de Vries, Johannes G.
Otten, Edwin
CHEMCATCHEM, 2018, 10 (13) : 2868 - 2872
[33] Recent application of oxa-Michael reaction in complex natural product synthesis
Hu, Jialei
Bian, Ming
Ding, Hanfeng
TETRAHEDRON LETTERS, 2016, 57 (50) : 5519 - 5539
[34] Asymmetric Organocatalytic Four-Component Quadruple Domino Reaction Initiated by Oxa-Michael Addition of Alcohols to Acrolein
Zhang, Fang-Lin
Xu, Ai-Wen
Gong, Yue-Fa
Wei, Mo-Hui
Yang, Xiang-Liang
CHEMISTRY-A EUROPEAN JOURNAL, 2009, 15 (28) : 6815 - 6818
[35] Oxa-Michael Addition Catalyzed by Amide-Based Acidic Ionic Liquids
Guo Hui
Wang Junliang
Li Xia
Lue Deshui
Lin Xianfu
CHINESE JOURNAL OF CATALYSIS, 2011, 32 (01) : 162 - 165
[36] Modular liquid crystal elastomer synthesis: Acid catalyzed oxa-Michael addition
Earl, Cameron
Kurji, Zuleikha
Kornfield, Julia
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2017, 253
[37] Organocatalytic oxa-Michael/Michael Addition/Deformylation Cascade Reaction of 3-Formylchromone with p-Quinol: Synthesis of the Furanochromanone Skeleton
Zheng, Xiurong
Chen, Jiajia
Li, Zhuowen
Zhong, Lin
Zhan, Ruoting
Huang, Huicai
ADVANCED SYNTHESIS & CATALYSIS, 2022, 364 (24) : 4402 - 4408
[38] Ionic liquid mediated Cu-catalyzed cascade oxa-Michael-oxidation: efficient synthesis of flavones under mild reaction conditions
Du, Zhiyun
Ng, Huifen
Zhang, Kun
Zeng, Huaqiang
Wang, Jian
ORGANIC & BIOMOLECULAR CHEMISTRY, 2011, 9 (20) : 6930 - 6933
[39] Anomalous reactivity of diphenylhydroxymethylphosphine oxide in the synthesis of a phosphorylated ether by oxa-Michael reaction
Cristau, HJ
Virieux, D
TETRAHEDRON LETTERS, 1999, 40 (04) : 703 - 706
[40] Construction of Multisubstituted Tetrahydropyrans by a Domino Oxa-Michael/Tsuji-Trost Reaction
Wang, Liang
Menche, Dirk
JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (23): : 10811 - 10823

← 1 2 3 4 5 →