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Asymmetric synthesis of syn hydroxyphenylalanine via aziridine ring expansion to an oxazoline

✍ Scribed by Giuliana Cardillo; Luca Gentilucci; Alessandra Tolomelli


Book ID
104262512
Publisher
Elsevier Science
Year
1999
Tongue
French
Weight
222 KB
Volume
40
Category
Article
ISSN
0040-4039

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✦ Synopsis


The synthesis of (2R,3S)-and (2S,3R)-hydroxyphenylalanine is reported. The main steps are the 1,4-addition of 0-benzylhydroxylamine to unsaturated imides and the ring expansion of truns-aziridines.


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From aziridines to carbapenems via a nov
✍ David Tanner; Peter Somfai πŸ“‚ Article πŸ“… 1988 πŸ› Elsevier Science 🌐 French βš– 431 KB

An enantioselective synthesis of the carbapenem antibiotic (+)-ps-5 is described. The starting point is the chiral Sharpless epoxyalcohol 2 which is transformed stereospecifically to the eziridine 6. Regioeelective ring-ope&ng of 6 by'LiEt Cu followed by RuQ oxidation yields the @-sulfonamide cat-bo