174502-72-8Relevant academic research and scientific papers
Synthesis of enantiomerically pure ω-amino acids by asymmetric α-alkylation of chiral ω-aminoalkyloxazolines
Rottmann, Antje,Liebscher, Juergen
, p. 359 - 362 (1996)
Enantiomerically pure α-alkyl-ω-aminocarboxylic acids 5, 6 and the correspodning α-alkyllactams 7 are synthesized starting from lactams 1 by ring transformation with a chiral aminoalcohol 2, asymmetric α-alkylation of the resulting 2-(ω-aminoalkyl)-oxazolines 3 and final hydrolysis.
Asymmetric synthesis of α-alkyl-ω-amino acids and α-alkyllactams
Rottmann, Antje,Bartoczek,Liebscher, Jürgen
, p. 313 - 327 (2007/10/03)
A versatile access to optically active α-branched ω-amino acids 8 and 9 and corresponding lactams 11 was developed allowing the synthesis of either enantiomer of these products. This asymmetric synthesis is based on amino alcohols 3 as chiral auxiliaries, which were converted to 2-(ω-benzenesulfonylaminoalkyl)oxazolines 4 by reaction with ω-amino-imido esters 2 or derivatives of lactams 1. The 2-(ω-benzenesulfonylaminoalkyl)oxazolines 4 were deprotonated by LDA and α-alkylated by alkyl halides 5. Final hydrolytic cleavage of the oxazoline ring afforded the amino acids 8 and 9 or lactams 11. The method does not follow Meyers model of α-alkylation of 2-alkyloxazolines and requires BEt3 as additive in order to achieve complete stereoselectivity.
