A New Approach to the Synthesis of  N ‐Alkylated 2‐Substituted Azetidin‐3‐ones | Zendy

Gérard Stéphane | Zendy; Raoul Marion | Zendy; Sapi Janos | Zendy

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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)

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