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Issue 11, 2014
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Asymmetric synthesis of N,O-heterocycles via enantioselective iridium-catalysed intramolecular allylic amidation

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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

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Supplementary files

Article information


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

Chem. Sci., 2014,5, 4216-4220
Article type
Edge Article

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

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