As part of our program aimed at the design of specific enzyme inhibitors, we have been interested in the synthesis of a-alkyl substituted-u-amino acids of type 1 (Y -H or heteroatom functions). R CH3 The classical route to a-alkyl substituted-a-amino acids consists of a Bucherer or a Strecker reacti
(S)-α-methyl,α-amino acids: a new stereocontrolled synthesis
✍ Scribed by Daniele Balducci; Ilaria Lazzari; Magda Monari; Fabio Piccinelli; Gianni Porzi
- Book ID
- 106221841
- Publisher
- Springer
- Year
- 2009
- Tongue
- English
- Weight
- 384 KB
- Volume
- 38
- Category
- Article
- ISSN
- 0939-4451
No coin nor oath required. For personal study only.
📜 SIMILAR VOLUMES
The diastereoselective synthesis of syn-a-alkyl a-hydroxy 13-amino acids 4a-h was easily accomplished by reaction of the sodium dianion of the corresponding anti a-alky113-benzoylamino acid methyl esters with iodine. The intermediate a-iodo derivatives spontaneously afforded c/s-oxazolines which, up
Deprotonation of alanine ester imines with KO'Bu in DMSO or DMF and alkylation of the formed enolates with several 2-fluoroalkyl halogenides 2 and subsequent hydrolysis of the imino and the ester groups are presented as an efficient three-step sequence for the synthesis of racemic title compounds 5.