Studies on enolate chemistry of 8-thiabicyclo[3.2.1]- octan-3-one: enantioselective deprotonation and synthesis of sulfur analogs of tropane alkaloids
β Scribed by Majewski, Marek; DeCaire, Marc; Nowak, Pawel; Wang, Fan
- Book ID
- 111960444
- Publisher
- NRC Research Press
- Year
- 2001
- Tongue
- French
- Weight
- 215 KB
- Volume
- 79
- Category
- Article
- ISSN
- 0008-4042
- DOI
- 10.1139/v01-157
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π SIMILAR VOLUMES
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
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