Issue 11, 2014

Asymmetric synthesis of N,O-heterocycles via enantioselective iridium-catalysed intramolecular allylic amidation

Abstract

Chiral N,O-heterocycles were synthesized in high yields and excellent enantioselectivity up to 97% ee via iridium-catalysed intramolecular allylic substitution with nucleophilic attack by the amide oxygen atom. The resulting benzoxazine derivatives were further transformed into challenging chiral N,O-ketals bearing both a tertiary and a quaternary center with excellent diastereoselectivities.

Graphical abstract: Asymmetric synthesis of N,O-heterocycles via enantioselective iridium-catalysed intramolecular allylic amidation

Supplementary files

Article information

Article type
Edge Article
Submitted
30 Jun 2014
Accepted
21 Jul 2014
First published
21 Jul 2014
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., 2014,5, 4216-4220

Asymmetric synthesis of N,O-heterocycles via enantioselective iridium-catalysed intramolecular allylic amidation

D. Zhao, M. Fañanás-Mastral, M. Chang, E. Otten and B. L. Feringa, Chem. Sci., 2014, 5, 4216 DOI: 10.1039/C4SC01940G

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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