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Alcaide B, Aly MF, Sierra MA. Stereoselective Synthesis of 3-Substituted 4-(Formyloxy)-2-azetidinones by the Unusual Baeyer-Villiger Reaction of beta-Lactam Aldehydes. Scope and Synthetic Applications. J Org Chem. 1996;61(25):8819-8825doi: 10.1021/jo9612685.
Alcaide, B., Aly, M. F., & Sierra, M. A. (1996). Stereoselective Synthesis of 3-Substituted 4-(Formyloxy)-2-azetidinones by the Unusual Baeyer-Villiger Reaction of beta-Lactam Aldehydes. Scope and Synthetic Applications. The Journal of organic chemistry, 61(25), 8819-8825. https://doi.org/10.1021/jo9612685
Alcaide, Benito, et al. "Stereoselective Synthesis of 3-Substituted 4-(Formyloxy)-2-azetidinones by the Unusual Baeyer-Villiger Reaction of beta-Lactam Aldehydes. Scope and Synthetic Applications." The Journal of organic chemistry vol. 61,25 (1996): 8819-8825. doi: https://doi.org/10.1021/jo9612685
Alcaide B, Aly MF, Sierra MA. Stereoselective Synthesis of 3-Substituted 4-(Formyloxy)-2-azetidinones by the Unusual Baeyer-Villiger Reaction of beta-Lactam Aldehydes. Scope and Synthetic Applications. J Org Chem. 1996 Dec 13;61(25):8819-8825. doi: 10.1021/jo9612685. PMID: 11667860.
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J Org Chem. 1996 Dec 13;61(25):8819-8825. doi: 10.1021/jo9612685.

Stereoselective Synthesis of 3-Substituted 4-(Formyloxy)-2-azetidinones by the Unusual Baeyer-Villiger Reaction of beta-Lactam Aldehydes. Scope and Synthetic Applications.

The Journal of organic chemistry

Benito Alcaide, Moustafa F. Aly, Miguel A. Sierra

Affiliations

  1. Departamento de Química Orgánica I, Facultad de Química, Universidad Complutense, 28040 Madrid, Spain.

PMID: 11667860 DOI: 10.1021/jo9612685

Abstract

The Baeyer-Villiger oxidation of 4-formyl-beta-lactams 1with m-CPBA gave 4-(formyloxy) beta-lactams 2 in a simple, efficient, and totally stereoselective process. This reaction is one of the scarce examples of the preferred migration of a carbon moiety in an aliphatic aldehyde. The influence of the substituents at N1 and C3 of the four-membered ring in the Baeyer-Villiger rearrangement has been studied. Thus, alkyl, alkenyl, aryl, and alkyloxy 3-substituted-1-(p-anisyl)-2-azetidinones 1 form exclusively 4-(formyloxy) beta-lactams 2. Amide or acetoxy substituents at C3 of the four-membered ring produce mixtures of 4-(formyloxy) beta-lactams 2and 4-carboxy beta-lactams 5. The exclusive formation of carboxy derivatives is observed sometimes for 1-alkyl-substituted-2-azetidinones 1. 4-(Formyloxy) beta-lactams 2 are suitable starting materials to prepare different 4-unsubstituted beta-lactams 9 using beta-hydroxy amides 8 as isolable intermediates. The overall transformation 4-formyl-2-azetidinone to 4-unsubstituted beta-lactam is an easy and convenient stereoselective route to these interesting types of compounds.

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