Nonracemic 5,6-disubstituted 2-piperidones were prepared from readily accessible 3,4-disubstituted-2-azetidinones having preinstalled substituents by reductive ring opening of 2-azetidinones followed by stereoselective installation of Z-a,b-unsaturated ester and lactam formation. For the synthetic a
Facile Conversion of 2-Azetidinones to 2-Piperidones: Application to a Formal Synthesis of Prosopis and Cassia Alkaloids.
β Scribed by Hyeon Kyu Lee; Jong Soo Chun; Chwang Siek Pak
- Publisher
- John Wiley and Sons
- Year
- 2003
- Weight
- 167 KB
- Volume
- 34
- Category
- Article
- ISSN
- 0931-7597
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2-Azetidinones were smoothly transformed to unsaturated ketones through the ring opening of activated 2-azetidinone by phosphonate stabilized carbanion and subsequent Horner-Wadsworth-Emmons olefination of the resulting b-ketophosphonates with aldehydes. A formal synthesis of L-erythro -sphingosine
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