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A New Approach to the Synthesis of N ‐Alkylated 2‐Substituted Azetidin‐3‐ones
Author(s) -
Gérard Stéphane,
Raoul Marion,
Sapi Janos
Publication year - 2006
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200500987
Subject(s) - chemistry , alkylation , intramolecular force , enantioselective synthesis , tandem , nucleophilic substitution , nucleophile , alkyl , combinatorial chemistry , organic chemistry , stereochemistry , medicinal chemistry , catalysis , materials science , composite material
We report a one‐pot methodology for the synthesis of N ‐alkylated 2‐substituted azetidin‐3‐ones based on a tandem nucleophilic substitution followed by intramolecular Michael reaction of primary amines with alkyl 5‐bromo‐4‐oxopent‐2‐enoates, obtained in turn in three steps from levulinic acid. A mechanistic interpretation of these reactions and an attempted enantioselective approach are also described. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)