Diastereoselective and regiodivergent oxa-[3 + 2] cycloaddition of Achmatowicz products and cyclic 1,3-dicarbonyl compounds

Jingxun Yu; Haichen Ma; Hongliang Yao; Hang Cheng; Rongbiao Tong

doi:10.1039/C6QO00034G

You do not have JavaScript enabled. Please enable JavaScript to access the full features of the site or access our non-JavaScript page.

Diastereoselective and regiodivergent oxa-[3 + 2] cycloaddition of Achmatowicz products and cyclic 1,3-dicarbonyl compounds†

Jingxun Yu,‡^a Haichen Ma,‡^a Hongliang Yao,^a Hang Cheng^a and Rongbiao Tong*^ab

Author affiliations

* Corresponding authors

^a Department of Chemistry, Hong Kong University of Science and Technology, Clearwater Bay, Kowloon, Hong Kong, China
E-mail: rtong@ust.hk

^b HKUST Shenzhen Research Institute, Shenzhen, China

Abstract

Development of two new protocols for oxa-[3 + 2] cycloaddition reactions of Achmatowicz products with 1,3-dicarbonyl compounds for rapid and highly efficient assembly of polycyclic furopyranones is described. Plausible mechanisms were proposed to involve either Pd-catalyzed Tsuji–Trost allylation and concomitant oxa-Michael cyclization or quinine-promoted cascade Michael addition and S_N2-type cycloacetalization.

This article is part of the themed collection: Celebrating the 75th Birthday of Professor Barry Trost

Download options Please wait...

Supplementary files

Article information

DOI: https://doi.org/10.1039/C6QO00034G
Article type: Research Article
Submitted: 21 Қаң. 2016
Accepted: 24 Нау. 2016
First published: 25 Нау. 2016

Download Citation

Org. Chem. Front., 2016,3, 714-719

Author version available

Download author version (PDF)

Permissions

Request permissions

Diastereoselective and regiodivergent oxa-[3 + 2] cycloaddition of Achmatowicz products and cyclic 1,3-dicarbonyl compounds

J. Yu, H. Ma, H. Yao, H. Cheng and R. Tong, Org. Chem. Front., 2016, 3, 714 DOI: 10.1039/C6QO00034G

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Social activity

Fetching data from CrossRef.
This may take some time to load.

Organic Chemistry Frontiers

Diastereoselective and regiodivergent oxa-[3 + 2] cycloaddition of Achmatowicz products and cyclic 1,3-dicarbonyl compounds†

Abstract

Supplementary files

Article information

Download Citation

Author version available

Permissions

Diastereoselective and regiodivergent oxa-[3 + 2] cycloaddition of Achmatowicz products and cyclic 1,3-dicarbonyl compounds

Social activity

Search articles by author

Spotlight

Advertisements