✦ LIBER ✦
Stereoselective synthesis of stable isotope-labeled L-α-amino acids: Electrophilic amination of Oppolzer's acyl sultams in the synthesis of L-[15N]alanine, L-[15N]valine, L-[15N]leucine, L-[15N]phenylalanine and L-[1-13C, 15N]valine
✍ Scribed by Siegfried N. Lodwig; Clifford J. Unkefer
- Publisher
- John Wiley and Sons
- Year
- 1996
- Tongue
- French
- Weight
- 475 KB
- Volume
- 38
- Category
- Article
- ISSN
- 0022-2135
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✦ Synopsis
Using 1 -chloro-l-[~~N]nitrosocyclohexane, we have prepared five L-[a-'SN]arnino acids.
The stereoselective electophillic hydroxyamination of (S)-acylbornane-l0,2-suftams, followed by ZnO/H+ reduction, and alkaline cleavage of the chiral auxiliary, gave the amino acids in 97.2-99.5 % e.e. By starting with labeled (S)acylbornane-l0,2-sultams this stereoselective route could be to prepare many 13C and/or 15N isotopomers of a-amino acids.