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)

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)

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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

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