Exploiting Organocatalysis: Enantioselective Synthesis of Vinyl Glycines by Allylic Sulfimide [2,3] Sigmatropic Rearrangement
Have it both ways: Enantiomerically enriched E vinyl glycines may be accessed from aldehydes in a concise sequence that combines an organocatalytic α sulfenylation, stereoselective olefination, a sulfimidation, and a [2,3] sigmatropic rearrangement (see scheme, Boc=tert‐butoxycarbonyl, nHex=n‐hexyl)...
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Veröffentlicht in: | Angewandte Chemie (International ed.) 2007-01, Vol.46 (28), p.5369-5372 |
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Hauptverfasser: | , , |
Format: | Artikel |
Sprache: | eng |
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Online-Zugang: | Volltext |
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Zusammenfassung: | Have it both ways: Enantiomerically enriched E vinyl glycines may be accessed from aldehydes in a concise sequence that combines an organocatalytic α sulfenylation, stereoselective olefination, a sulfimidation, and a [2,3] sigmatropic rearrangement (see scheme, Boc=tert‐butoxycarbonyl, nHex=n‐hexyl). Either enantiomeric series can be accessed by control of the alkene geometry in the olefination step. |
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ISSN: | 1433-7851 1521-3773 |
DOI: | 10.1002/anie.200701459 |