Synthesis of optically active azetidine-2,4-dicarboxylic acid and related chiral auxiliaries for asymmetric synthesis
1995; Issue: 6 Linguagem: Inglês
10.1039/p19950000693
ISSN2050-8255
AutoresJun'ichi Hoshino, Junko Hiraoka, Yasuo Hata, Seiji Sawada, Yukio Yamamoto,
Tópico(s)Asymmetric Hydrogenation and Catalysis
Resumo(S)-1-Phenylethylamine has been used as a chiral auxiliary as well as a nitrogen atom donor in the synthesis of an enantiomeric pair of azetidine-2,4-dicarboxylic acids, the absolute configuration of one of which has been assigned on the basis of the X-ray structure and the known absolute configuration of the (S)-1-phenylethylamine moiety. Chiral auxiliaries of related C2-symmetric azetidines have also been prepared and their propionamides have been asymmetrically alkylated. The stereochemistry of the resulting products was compared with their analogues having different ring sizes.
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