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Enantioselective deprotonation of the 8-oxabicyclo[3.2.1]octan-3-one: Synthesis of 8-oxa-norcocaines and 8-oxa-pseudonorcocaines

✍ Scribed by Daniele Simoni; Marinella Roberti; Riccardo Rondanin; Alan P. Kozikowski

Book ID
104261546
Publisher
Elsevier Science
Year
1999
Tongue
French
Weight
213 KB
Volume
40
Category
Article
ISSN
0040-4039

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✦ Synopsis

The enantioselective deprotonation of the 8-oxabicyclo[3.2. l]octan-3-one with chiral lithium amides 5 and 6, in the presence of LiC1, gave the chiral lithium enolates which were in turn reacted with methyl cyanoformate. The resulting chiral [3-keto esters were reduced with sodium amalgam to afford the 8-oxa-ecgonine-and 8-oxa-pseudoecgonine-like derivatives which allowed facile preparation of the (+)-and (-)-8-oxa-norcocaines and (+)-and (-)-8-oxa-pseudonorcocaines. The new synthesized 8-oxa analogues of cocaine showed good enantiomeric excesses in the range of 84-90%.

πŸ“œ SIMILAR VOLUMES

ChemInform Abstract: Enantioselective De
ChemInform Abstract: Enantioselective Deprotonation of the 8-Oxabicyclo[3.2.1]octan-3-one: Synthesis of 8-Oxa-norcocaines and 8-Oxa-pseudonorcocaines.
✍ Daniele Simoni; Marinella Roberti; Riccardo Rondanin; Alan P. Kozikowski πŸ“‚ Article πŸ“… 2010 πŸ› John Wiley and Sons βš– 35 KB πŸ‘ 1 views

Enantioselective Deprotonation of the 8-Oxabicyclo[3.2.1]octan-3-one: Synthesis of 8-Oxa-norcocaines and 8-Oxa-pseudonorcocaines. -Asymmetric deprotonation of the racemic ketone (I) using chiral lithium amides provides ready access to the non-racemic Ξ²-ketoesters (III), which can be easily transfor