Multi‐gram scale synthesis of chiral 3‐methyl‐2,5‐trans‐tetrahydrofurans

Qin, S., Cao, Y., Luo, Y., Jiang, S., Clark, J. S. , Wang, X. and Yang, G. (2019) Multi‐gram scale synthesis of chiral 3‐methyl‐2,5‐trans‐tetrahydrofurans. Helvetica Chimica Acta, 102(7), e1900131. (doi: 10.1002/hlca.201900131)

Abstract

In this article, we report the rapid and facile synthesis of chiral 3‐methyl‐2,5‐trans‐tetrahydrofurans. This reaction utilizes cheap and easily available starting materials. A domino hydrolysis and intramolecular Michael‐type ring closure reaction was the key step. As a result, synthesis of the desired 3‐methyl‐2,5‐trans‐tetrahydrofurans could be achieved in gram‐scale over seven linear steps with high chemical yield and high diastereoselectivity.

• Item Type: Articles
• Additional Information: Funding Information: National Natural Science Foundation of China. Grant Numbers: 81703343, 81503019, Fundamental Research Funds for the Central Universities,Tianjin Science and Technology Project. Grant Number: 17PTSYJC00070.
• Status: Published
• Refereed: Yes
• Glasgow Author(s) Enlighten ID: Clark, Professor Stephen
• Authors: Qin, S., Cao, Y., Luo, Y., Jiang, S., Clark, J. S., Wang, X., and Yang, G.
• College/School: College of Science and Engineering > School of Chemistry
• Journal Name: Helvetica Chimica Acta
• Publisher: Wiley
• ISSN: 0018-019X
• ISSN (Online): 1522-2675
• Published Online: 03 July 2019
• Copyright Holders: © 2019 Wiley‐VHCA AG, Zurich, Switzerland
• First Published: First published in Helvetica Chimica Acta 102(7):e1900131
• Publisher Policy: Reproduced in accordance with the publisher copyright policy