A facile synthesis of 3-substituted pipecolic acids, chimeric amino acids
β Scribed by Gergely M. Makara; Garland R. Marshall
- Publisher
- Elsevier Science
- Year
- 1997
- Tongue
- French
- Weight
- 247 KB
- Volume
- 38
- Category
- Article
- ISSN
- 0040-4039
No coin nor oath required. For personal study only.
β¦ Synopsis
Three protected 3-substituted pipecolic acid analogs were prepared as constrained chimeric amino acid building blocks. The concise synthetic route enables the synthesis of other derivatives with sidechaln functionality of amino acids as well.
π SIMILAR VOLUMES
A new general method for the preparation of 2-alkyl-pipecolic acids has been developed. The syntheses of 2-methyl-, 2-benzyl-and cis-6-methylpipecolic acids are described. (-)S-and (+)R-2-methylpipecolic acids were resolved by fractional crystallization of the quinine salt of their N-carbobenzoxy de
The Michael addition of R2CuLi or R2CuMgBr to 4-phenyl-3,4,7,8-tetrahydro-6H-pyrido (2, l-c)(1,4)oxazin-1-one 2, readily obtained from 2-cyano-6-phenyloxazolopiperidine 1, led to the formation of alkylated lactones 4a-d in high yield and with complete diastereoselectivity. Transformation of lactones
A lacile slereoselcctive melhod Ior the synthesis of y-substituted, y-mnino acids from of amino acids was developed. The key step of the procedurc is complete reduction of Ihe keto functionality of ot-~unino acyl Meldruln's acid by sodium acetoxyborohydride. The resulting amino alkyl Meldrum's acid