Anwendung von N‐Tritylmethionin zur Darstellung von biologisch und synthetisch interessanten Heterocyclen
- 14 December 1988
- journal article
- research article
- Published by Wiley in European Journal of Organic Chemistry
- Vol. 1988 (12) , 1127-1133
- https://doi.org/10.1002/jlac.198819881204
Abstract
N‐Tritylmethionin‐Derivate liefern durch Überführung in Methylsulfonium‐Salze und anschließende Einwirkung von Natriumhydrid oder Kalium‐tert‐butylat die Heterocyclen N‐(Trityl‐L‐homoserinlacton (3), (S)‐ bzw. (R)‐3‐(N‐Tritylamino)tetrahydrofuran (7a, 7b), (S)‐1‐Hydroxy‐3‐(N‐tritylamino)‐2‐pyrrolidinon (14), (S)‐4‐(N‐Tritylamino)‐1,2‐oxazinan‐3‐on (15), (S)‐3‐(N‐Tritylamino)‐2‐pyrrolidon (23), (S)‐1‐tert‐Butyloxycarbonylamino‐3‐(N‐tritylamino)‐2‐pyrrolidon (27) und (S)‐2‐Methyl‐4‐(N‐tritylamino)‐1,2‐oxazinan‐3‐on (18). Durch Methylierung von 14 und 15 erhält man (S)‐1‐Methoxy‐3‐(N‐tritylamino)‐2‐pyrrolidon (17) bzw. 18. Die Stereochemie der Verbindungen 3, 7a und 17 wird durch Röntgenstrukturanalyse ermittelt.Keywords
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