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

Depeng Zhao; Martin Fananas-Mastral; Mu-Chieh Chang; Edwin Otten; Ben L. Feringa

doi:10.1039/c4sc01940g

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

Depeng Zhao, Martin Fananas-Mastral, Mu-Chieh Chang, Edwin Otten, Ben L. Feringa

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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.

Original language	English
Pages (from-to)	4216-4220
Number of pages	5
Journal	Chemical Science
Volume	5
Issue number	11
DOIs	https://doi.org/10.1039/c4sc01940g
Publication status	Published - 1-Oct-2014

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Asymmetric synthesis of N,O-heterocycles via enantioselective iridium-catalysed intramolecular allylic amidationFinal publisher's version, 311 KBLicence: Unspecified
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CCDC 957090: Experimental Crystal Structure Determination
Zhao, D. (Contributor), Fananas Mastral, M. (Contributor), Chang, M.-C. (Contributor), Otten, E. (Contributor) & Feringa, B. L. (Contributor), University of Groningen, 22-Aug-2013
DOI: 10.5517/cc113xwy
Dataset
CCDC 957091: Experimental Crystal Structure Determination
Zhao, D. (Contributor), Fananas Mastral, M. (Contributor), Chang, M.-C. (Contributor), Otten, E. (Contributor) & Feringa, B. L. (Contributor), University of Groningen, 22-Aug-2013
DOI: 10.5517/cc113xxz
Dataset

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title = "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.",

author = "Depeng Zhao and Martin Fananas-Mastral and Mu-Chieh Chang and Edwin Otten and Feringa, {Ben L.}",

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T1 - Asymmetric synthesis of N,O-heterocycles via enantioselective iridium-catalysed intramolecular allylic amidation

AU - Zhao, Depeng

AU - Fananas-Mastral, Martin

AU - Chang, Mu-Chieh

AU - Otten, Edwin

AU - Feringa, Ben L.

N1 - PT: J; TC: 0; UT: WOS:000343004300013

PY - 2014/10/1

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N2 - 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.

AB - 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.

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DO - 10.1039/c4sc01940g

M3 - Article

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JO - Chemical Science

JF - Chemical Science

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ER -

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

Abstract

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CCDC 957090: Experimental Crystal Structure Determination

CCDC 957091: Experimental Crystal Structure Determination

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