Issue 4, 2017
From the journal:

Chemical Science

Rhodium(i)-catalyzed stereoselective [4+2] cycloaddition of oxetanols with alkynes through C(sp3)–C(sp3) bond cleavage†

Rui Guo,‡ab   Xinxin Zheng,‡c   Dayong Zhang*c  and  Guozhu Zhang ORCID logo *ab  

* Corresponding authors

a State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, P. R. China
E-mail: guozhuzhang@sioc.ac.cn

b University of Chinese Academy of Sciences, Beijing, China

c Institute of Pharmaceutical Science, China Pharmaceutical University, Nanjing, P. R. China
E-mail: cpuzdy@163.com

Abstract

An efficient and convenient synthesis of highly functionalized dihydropyrans has been achieved through rhodium(I)-catalysed tandem C(sp3)–C(sp3) bond cleavage and annulation of oxetanols with alkynes. An enantioselective version was enabled using a Binaphine ligand. Excellent site-selectivity and remarkable enantioretention are obtained for 2-substituted oxetanols.

Graphical abstract: Rhodium(i)-catalyzed stereoselective [4+2] cycloaddition of oxetanols with alkynes through C(sp3)–C(sp3) bond cleavage

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Article information

DOI
https://doi.org/10.1039/C6SC05246K
Article type
Edge Article
Submitted
30 Nov 2016
Accepted
22 Jan 2017
First published
23 Jan 2017
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY license

Chem. Sci., 2017,8, 3002-3006

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Rhodium(I)-catalyzed stereoselective [4+2] cycloaddition of oxetanols with alkynes through C(sp3)–C(sp3) bond cleavage

R. Guo, X. Zheng, D. Zhang and G. Zhang, Chem. Sci., 2017, 8, 3002 DOI: 10.1039/C6SC05246K

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

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