57043-01-3Relevant articles and documents
Radical cyclization in heterocycle synthesis. Part 13: Sulfanyl radical addition-cyclization of oxime ethers and hydrazones connected with alkenes for synthesis of cyclic β-amino acids
Miyata, Okiko,Muroya, Kanami,Kobayashi, Tomoko,Yamanaka, Rina,Kajisa, Seiko,Koide, Junko,Naito, Takeaki
, p. 4459 - 4479 (2002)
A combination of sulfanyl radical addition-cyclization of the oxime ethers and hydrazones connected with alkenes and subsequent conversion of a phenylsulfanylmethyl group to a carboxyl group provides a novel method for the construction of the cyclic β-amino acids. Upon treatment with thiophenol in the presence of AIBN, the oxime ethers and hydrazones smoothly underwent sulfanyl radical addition-cyclization to give the 2-(phenylsulfanylmethyl)cycloalkylamine. This method was successfully applied to the practical synthesis of 2-aminocyclopentanecarboxylic acid and 4-amino-3-pyrrolidinecarboxylic acid.
Synthesis of novel sila-substituted β-amino acids
Matthews, Jennifer L,McArthur, Duncan R,Muir, Kenneth W
, p. 5401 - 5404 (2007/10/03)
A highly efficient and stereoselective synthesis of unnatural cyclic sila-substituted β-amino acids has been developed from simple starting materials. The key step is nucleophilic ring opening of an intermediate aziridine with an umpolung synthon for the
An improved synthesis of enantiopure β-amino acids
Cimarelli,Palmieri,Volpini
, p. 2943 - 2953 (2007/10/03)
An improved method for the preparation of both the enantiopure β-amino acids is presented. The diastereomer benzyl β-amino esters, obtained by stereoselective reduction of β-enamino esters, were separated and hydrogenolyzed to the free enantiopure β-amino acids.
