Issue 9, 2017

Asymmetric syntheses of 8-oxabicyclo[3,2,1]octane and 11-oxatricyclo[5.3.1.0]undecane from glycals

Abstract

Herein, we describe an efficient method to prepare enantiomerically pure 8-oxabicyclo[3.2.1]octanes via gold(I)-catalyzed tandem 1,3-acyloxy migration/Ferrier rearrangement of glycal derived 1,6-enyne bearing propargylic carboxylates. The resultant compounds could then undergo interrupted Nazarov cyclization to afford diastereomerically pure 11-oxatricyclo[5.3.1.0]undecanes.

Graphical abstract: Asymmetric syntheses of 8-oxabicyclo[3,2,1]octane and 11-oxatricyclo[5.3.1.0]undecane from glycals

Supplementary files

Article information

Article type
Edge Article
Submitted
12 Jun 2017
Accepted
31 Jul 2017
First published
07 Aug 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, 6656-6661

Asymmetric syntheses of 8-oxabicyclo[3,2,1]octane and 11-oxatricyclo[5.3.1.0]undecane from glycals

H. Liao, W. Leng, K. Le Mai Hoang, H. Yao, J. He, A. Y. H. Voo and X. Liu, Chem. Sci., 2017, 8, 6656 DOI: 10.1039/C7SC02625K

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.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements