- Diastereoselective functionalisation of Baylis-Hillman adducts: A convenient approach to α-methyl-α-amino acids
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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.
- Martelli, Gianluca,Orena, Mario,Rinaldi, Samuele,Sabatino, Piera
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experimental part
p. 489 - 497
(2010/11/04)
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- Synthesis of unsaturated β-amino acid derivatives from carbamates of the Baylis-Hillman products
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By treatment with a catalytic amount of DBU in DCM, N-p-toluenesulphonyl carbamates 6a-c, prepared starting from the corresponding Baylis-Hillman adducts, gave (E)-2-(p-toluenesulphonylaminomethyl)propenoates 3a-c, exclusively. On the contrary, changing D
- Ciclosi, Marco,Fava, Cristiana,Galeazzi, Roberta,Orena, Mario,Sepulveda-Arques, José
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p. 2199 - 2202
(2007/10/03)
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