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Facile Transformation of 2-Azetidinones to Unsaturated Ketones: Application to the Formal Synthesis of Sphingosine and Phytosphingosine.

✍ Scribed by Hyeon Kyu Lee; Eun-Kyung Kim; Chwang Siek Pak

Publisher
John Wiley and Sons
Year
2003
Weight
168 KB
Volume
34
Category
Article
ISSN
0931-7597

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Facile transformation of 2-azetidinones
Facile transformation of 2-azetidinones to unsaturated ketones: application to the formal synthesis of sphingosine and phytosphingosine
✍ Hyeon Kyu Lee; Eun-Kyung Kim; Chwang Siek Pak πŸ“‚ Article πŸ“… 2002 πŸ› Elsevier Science 🌐 French βš– 149 KB

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

Facile conversion of 2-azetidinones to 2
Facile conversion of 2-azetidinones to 2-piperidones: application to a formal synthesis of Prosopis and Cassia alkaloids
✍ Hyeon Kyu Lee; Jong Soo Chun; Chwang Siek Pak πŸ“‚ Article πŸ“… 2003 πŸ› Elsevier Science 🌐 French βš– 249 KB

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