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Issue 34, 2016
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Enantioselective isothiourea-catalysed trans-dihydropyridinone synthesis using saccharin-derived ketimines: scope and limitations

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Abstract

The catalytic enantioselective synthesis of a range of trans-dihydropyridinones from aryl-, heteroaryl- and alkenylacetic acids and saccharin-derived ketimines with good to excellent stereocontrol (15 examples, up to >95 : 5 dr, up to >99 : 1 er) is reported. After extensive optimisation, HyperBTM proved the optimal isothiourea catalyst for this transformation at −78 °C, giving trans-dihydropyridones with generally excellent levels of diastereo- and enantioselectivity.

Graphical abstract: Enantioselective isothiourea-catalysed trans-dihydropyridinone synthesis using saccharin-derived ketimines: scope and limitations

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Article information


Submitted
12 Jul 2016
Accepted
26 Jul 2016
First published
26 Jul 2016

This article is Open Access

Org. Biomol. Chem., 2016,14, 8068-8073
Article type
Paper

Enantioselective isothiourea-catalysed trans-dihydropyridinone synthesis using saccharin-derived ketimines: scope and limitations

D. G. Stark, C. M. Young, T. J. C. O'Riordan, Alexandra. M. Z. Slawin and A. D. Smith, Org. Biomol. Chem., 2016, 14, 8068
DOI: 10.1039/C6OB01473A

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