Stereodivergent synthesis of 1,3-syn- and -anti-tetrahydropyrimidinones
An efficient protocol for the stereoselective synthesis of 1,3-syn and -anti-tetrahydropyrimidinones (syn- and anti-11a) is reported. The modular procedure is based on a stereodivergent cyclization of readily available urea-type substrates (10a) by intramolecular allylic substitution. The cyclizatio...
Gespeichert in:
| Hauptverfasser: | , , , |
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| Dokumenttyp: | Article (Journal) |
| Sprache: | Englisch |
| Veröffentlicht: |
15 October 2010
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| In: |
Organic letters
Year: 2010, Jahrgang: 12, Heft: 20, Pages: 4494-4497 |
| ISSN: | 1523-7052 |
| DOI: | 10.1021/ol101755m |
| Online-Zugang: | Verlag, lizenzpflichtig, Volltext: https://doi.org/10.1021/ol101755m
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| Verfasserangaben: | Michael Morgen, Sebastian Bretzke, Pengfei Li, and Dirk Menche |
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| 520 | |a An efficient protocol for the stereoselective synthesis of 1,3-syn and -anti-tetrahydropyrimidinones (syn- and anti-11a) is reported. The modular procedure is based on a stereodivergent cyclization of readily available urea-type substrates (10a) by intramolecular allylic substitution. The cyclization proceeds with excellent yield (up to 99%) and selectivity (up to dr > 20:1), purely based on substrate control. The product pyrimidines can be readily transformed into the corresponding free syn- and anti-amines. | ||
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