Next Article in Journal
Evaluation of Marine Microalga Diacronema vlkianum Biomass Fatty Acid Assimilation in Wistar Rats
Next Article in Special Issue
Special Issue: Asymmetric Synthesis 2017
Previous Article in Journal
Kinetics, Mechanism and Theoretical Studies of Norbornene-Ethylene Alternating Copolymerization Catalyzed by Organopalladium(II) Complexes Bearing Hemilabile α-Amino–pyridine
Previous Article in Special Issue
Recent Advances in Substrate-Controlled Asymmetric Cyclization for Natural Product Synthesis
Article Menu
Issue 7 (July) cover image

Export Article

Open AccessArticle
Molecules 2017, 22(7), 1096; doi:10.3390/molecules22071096

Enantioselective Michael Addition of Cyclic β-Diones to α,β-Unsaturated Enones Catalyzed by Quinine-Based Organocatalysts

1
College of Chemistry and Environment Protection Engineering, Southwest Minzu University, Chengdu 610041, China
2
Faculty of Geosciences and Environmental Engineering, Southwest Jiaotong University, Chengdu 610031, China
*
Author to whom correspondence should be addressed.
Received: 16 May 2017 / Revised: 25 June 2017 / Accepted: 26 June 2017 / Published: 30 June 2017
(This article belongs to the Special Issue Asymmetric Synthesis 2017)
View Full-Text   |   Download PDF [1645 KB, uploaded 3 July 2017]   |  

Abstract

An enantioselective (52–98% ee) Michael addition between cyclic β-diones and α,β-unsaturated enones was established in the presence of quinine-based primary amine or squaramide. A variety of cinnamones were smoothly converted into the desired 3,4-dihydropyrans in moderate to high yields (63–99%). Chalcones were also suitable acceptors and gave rise to the expected adducts in satisfactory yields (31–99%). The resulting adducts readily underwent further modification to form fused 4H-pyran or 2,3-dihydrofuran. View Full-Text
Keywords: cyclic β-dione; cinnamone; chalcone; michael addition; enantioselective cyclic β-dione; cinnamone; chalcone; michael addition; enantioselective
Figures

This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

Supplementary material

Scifeed alert for new publications

Never miss any articles matching your research from any publisher
  • Get alerts for new papers matching your research
  • Find out the new papers from selected authors
  • Updated daily for 49'000+ journals and 6000+ publishers
  • Define your Scifeed now

SciFeed Share & Cite This Article

MDPI and ACS Style

Wang, Q.; Wang, W.; Ye, L.; Yang, X.; Li, X.; Zhao, Z.; Li, X. Enantioselective Michael Addition of Cyclic β-Diones to α,β-Unsaturated Enones Catalyzed by Quinine-Based Organocatalysts. Molecules 2017, 22, 1096.

Show more citation formats Show less citations formats

Note that from the first issue of 2016, MDPI journals use article numbers instead of page numbers. See further details here.

Related Articles

Article Metrics

Article Access Statistics

1

Comments

[Return to top]

Molecules EISSN 1420-3049 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert
Back to Top