Issue 6, 2016
From the journal:

Organic Chemistry Frontiers

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 Chenga  and  Rongbiao Tong*ab  

* 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 SN2-type cycloacetalization.

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

About
Cited by
Related
Download options Please wait...

Supplementary files

Article information

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

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.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements