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
A simple route to the 8-oxabicyclo[3.2.1]octyl and 9-oxabicyclo[3.3.1]nonyl systems. Synthesis of the 8-oxa analog of cocaine.
β Scribed by Peter Brownbridge; Tak-Hang Chan
- Book ID
- 104237960
- Publisher
- Elsevier Science
- Year
- 1979
- Tongue
- French
- Weight
- 357 KB
- Volume
- 20
- Category
- Article
- ISSN
- 0040-4039
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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. -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
## Abstract The development and design of reliable and efficient methods for the construction of chiral building blocks are crucial in modern natural product synthesis. 8βOxabicyclo[3.2.1]octβ6βenβ3βones are readily accessible scaffolds with defined stereochemical features which have been exploited