A facile synthesis of chiral N-protected β-amino alcohols.
✍ Scribed by Marc Rodriguez; Muriel Llinares; Sylvie Doulut; Annie Heitz; Jean Martinez
- Publisher
- Elsevier Science
- Year
- 1991
- Tongue
- French
- Weight
- 211 KB
- Volume
- 32
- Category
- Article
- ISSN
- 0040-4039
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✦ Synopsis
Chiral N-protected p-amino alcohols are easily obtained by NaB& reduction of mixed anhydndes of N-protected a-ammo acids m an organic/aqueous medium. The alcohols obtamed from side chain or main chain reduction of N-protected asparhc acid are converted in good yields into lactones.
📜 SIMILAR VOLUMES
A facile synthesis of a wide variety of N-protected p-amino akobol derivatives under mild conditions is described. N-umtbane proceded amino acid N-carboxyanhydrides (UNCAs) were used as starting ma&al and reduced into the correspooding akohols with the appropriate hydride, sodium borobydride. The re
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~arnino alcohols are selectivelyN-thioscylatedby N-(thioacyl)phthalimidesunder very mild conditions to provide N-(hydroxyethyl)thiosmidesin high yields. CycMehydration with Burgess reagent then provides a-amino acid thiazolines. This approach provides a convenientattereative to those baaed upon rfri