Highly efficient synthesis of tetrasubstituted 2,3-dihydropyrans by three-component 'one-pot' reaction

被引：2

作者：

Li, Chao ^{[1
]}

Cai, Liang-Zhen ^{[1
]}

Liu, Xiao-Dong ^{[1
]}

Zhu, Shi-Zheng ^{[2
]}

Xing, Chun-Hui ^{[2
]}

Lu, Long ^{[2
]}

机构：

[1] E China Univ Sci & Technol, Sch Chem & Mol Engn, 130 Meilong Rd, Shanghai 200237, Peoples R China

[2] Chinese Acad Sci, Shanghai Inst Organ Chem, Key Lab Organofluorine Chem, 345 Lingling Rd, Shanghai 200032, Peoples R China

来源：

TETRAHEDRON LETTERS | 2016年 / 57卷 / 20期

基金：

中国国家自然科学基金;

关键词：

Dihydropyran; Perfluoroalkanesulfone; alpha; beta-Unsaturated ketone; Hetero Diels-Alder reaction; Three-component; DIELS-ALDER REACTIONS; BETA-KETO SULFONES; ASYMMETRIC-SYNTHESIS;

D O I：

10.1016/j.tetlet.2016.04.008

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

With ammonium acetate as catalyst, three-component 'one-pot' reaction of beta-keto perfluoroalkanesulfones, aldehydes, and vinyl ethers proceeded smoothly and afforded tetrasubstituted 2,3-dihydropyrans in moderate to excellent yields. Both aromatic and aliphatic aldehydes, as well as cyclic vinyl ether are compatible with this methodology. All dihydropyran products were obtained as cis- and trans-diastereomeric mixtures. The relative configurations were established by comparing the coupling constants of anomeric protons of both isomers and confirmed by single-crystal X-ray diffraction analysis. (C) 2016 Elsevier Ltd. All rights reserved.

引用

页码：2171 / 2174

页数：4

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