RSS-Feed abonnieren
Bitte kopieren Sie die angezeigte URL und fügen sie dann in Ihren RSS-Reader ein.
https://www.thieme-connect.de/rss/thieme/de/10.1055-s-00000131.xml
Synfacts 2011(1): 0092-0092
DOI: 10.1055/s-0030-1259181
DOI: 10.1055/s-0030-1259181
Organo- and Biocatalysis
© Georg Thieme Verlag
Stuttgart ˙ New York
Cinchona Amino-Thiocarbamate Catalyzed Bromolactonization
L. Zhou, C. K. Tan, X. Jiang, F. Chen, Y.-Y. Yeung*
National University of Singapore, Singapore
Weitere Informationen
Publikationsverlauf
Publikationsdatum:
21. Dezember 2010 (online)
Significance
A cinchonine-derived thiocarbamate is reported to efficiently catalyze the bromolactonization of 4-substituted 4-pentenoic acids to give the corresponding γ-lactones in high yields and good enantioselectivities. Catalyst 1 is presumed to act as a bifunctional catalyst, simultaneously activating NBS with the Lewis-basic thiocarbamate and the carboxylic acid with the Brønsted-basic tertiary amine. The utility of the products is demonstrated and initial mechanistic studies, supporting the suggested bifunctional mechanism, are provided.