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Enantioselective oxidation of thioethers: synthesis of trans-2-N,N-dialkylacetamide-1,3-dithiolanes-S-oxide and their use in asymmetric aldol-type reactions

โœ Scribed by Martina Corich; Fulvio Di Furia; Giulia Licini; Giorgio Modena


Publisher
Elsevier Science
Year
1992
Tongue
French
Weight
139 KB
Volume
33
Category
Article
ISSN
0040-4039

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โœฆ Synopsis


trans-Z-NN-dialkylacetamide-1,3-dith 2 have been obtained in high d.e. (>9!kl) and e.e. (up to 94%. >98% after crystallization) by enantioselective oxidation [Ti(i-PrOId. (+)-DET, r-BuOOH]. The aldol-type addition of the magnesium enolate of the N,Ndiethyl derivative (-)-2b to Lso-butyraldehyde affonied good chemical yields of a single diastereomer.


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