Asymmetric synthesis of (−)-(2R, 6R)-2,6-dimethylmorpholine
✍ Scribed by Emanuela Licandro; Stefano Maiorana; Antonio Papagni; Mary Pryce; Antonio Zanotti Gerosa; Sergio Riva
- Publisher
- Elsevier Science
- Year
- 1995
- Tongue
- English
- Weight
- 216 KB
- Volume
- 6
- Category
- Article
- ISSN
- 0957-4166
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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
Sch611kopf's auxiliary 16 was added to bis-lactim iodide 21 to give 1,2-bis[(3S,6R)-3,6dihydro-2,5-dimethoxy-3-isopropylpyrazin-6-yl]ethane 22 in 50% d,e. Dimer 22 was separated from its diastereoisomer 23 and deprotected using 6M HCI to afford homochiral (2R,5R)-2,5-diaminohexan-1,6dioic acid 24.