Enantioselective synthesis of (R)-and (S)-α-aminoacids using (6S)- and (6R)-6-methyl-morpholine-2,5-dione derivatives
✍ Scribed by Gianni Porzi; Sergio Sandri
- Book ID
- 108036376
- Publisher
- Elsevier Science
- Year
- 1996
- Tongue
- English
- Weight
- 336 KB
- Volume
- 7
- Category
- Article
- ISSN
- 0957-4166
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## Abstract The hydrogenation of 2′, 3′‐__O__‐isopropylidene‐5‐methyluridine **(1)** in water over 5% Rh/Al~2~O~3~ gave (5 __R__)‐ and (5 __S__)‐5‐methyl‐5, 6‐dihydrouridine **(2)**, separated as 5′‐__O__‐(__p__‐tolylsulfonyl)‐ **(3)** and 5′‐__O__‐benzoyl‐ **(5)** derivatives by preparative TLC. o
The title compounds were prepared via two efficient routes. The first sequence utilized a diastereospecific triflate alkylation in the key bond forming step while the second method relied on a novel intramolecular Mitsunobu reaction to set the required stereochemistry. Many pharmaceutical agents co