1032297-50-9Relevant academic research and scientific papers
Diastereoselective functionalisation of Baylis-Hillman adducts: A convenient approach to α-methyl-α-amino acids
Martelli, Gianluca,Orena, Mario,Rinaldi, Samuele,Sabatino, Piera
experimental part, p. 489 - 497 (2010/11/04)
The N-tosyl carbamates 4a-e, easily prepared starting from the Baylis-Hillman adducts 3a-e, underwent cyclization carried out with I 2/NIS in the presence of NaH, to give the corresponding 2-oxo-1,3-oxazolidines 5a-e in good yield and total stereoselection when the substituent at C-5 is Ar. After the removal of tosyl group, followed by the cleavage of the heterocyclic ring, the α-methyl-α-amino acids 8a,b and 10 were obtained in good yield as hydrochlorides. Springer-Verlag 2010.
Asymmetric organocatalysed [1,3]-sigmatropic rearrangements
Kobbelgaard, Sara,Brandes, Sebastian,Jorgensen, Karl Anker
experimental part, p. 1464 - 1471 (2009/04/04)
The first organocatalysed enantioselective [1,3]-sigmatropic O- to N-rearrangement reactions are presented. The reactions take place under regio- and enantioselective control, and are catalysed by cinchona alkaloids. Two reactions have been developed the first one is the rearrangement of imidates to amides, while the other rear rangement occurs from carbamates to amines via a decarboxylation. Both transformations give nitrogen protected β-amino acid derivatives as the product. These novel asymmetric organocatalysed [1,3]-sigmatropic O- to N-rearrangement reactions provide a reliable and efficient synthetic method for obtaining enantioenriched β-amino acid derivates in good yield from racemic starting materials.
