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 2006(12): 1282-1282
DOI: 10.1055/s-2006-949503
DOI: 10.1055/s-2006-949503
Organo- and Biocatalysis
© Georg Thieme Verlag Stuttgart · New York
l-Prolinamide-Catalyzed Enantioselective Synthesis of α-Hydroxyphosphonates
R. Dodda, C.-G. Zhao*
University of Texas at San Antonio, USA
Weitere Informationen
Publikationsverlauf
Publikationsdatum:
22. November 2006 (online)
Significance
The first organocatalytic cross aldol reaction of ketones with diethyl formylphosphonate hydrate is reported. In the presence of readily available l-prolinamide as catalyst, secondary α-hydroxyphosphonates have been synthesized in moderate to good yields (up to 95%), good diastereoselectivity (up to 95:5) and high enantiomeric ratios (up to >99:1). Besides acetone, other unsubstituted aliphatic ketones also participate in this reaction, however with a lower reactivity. Substituted or cyclic ketones may also be used for this cross aldol reaction.