ISSN:
0170-2041
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Description / Table of Contents:
Application of N-Tritylmethionine in the Preparation of Heterocycles of Biological and Synthetic InterestTreatment of the methylsulfonium salts of the corresponding N-tritylmethionine derivatives with sodium hydride or potassium tert-butoxide provides the heterocycles N-trityl-L-homoserine lactone (3), (S)- and (R)-3-(N-tritylamino)tetrahydrofuran (7a, 7b), (S)-1-hydroxy-3-(N-tritylamino)-2-pyrrolidinone (14), (S)-4-(N-tritylamino)-1,2-oxazinan-3-one (15), (S)-3-(N-tritylamino)-2-pyrrolidone (23), (S)-1-tert-butyloxycarbonylamino-3-(N-tritylamino)-1,2-oxazinan-3-one (18). Methylation of 14 and 15 yields (S)-1-methoxy-3-(N-tritylamino)-2-pyrrolidone (17) and 18, respectively. The stereochemistry of compounds 3, 7a, and 17 has been determined by X-ray crystal structure analysis.
Notes:
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.
Additional Material:
3 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/jlac.198819881204
Permalink