184423-89-0Relevant academic research and scientific papers
Stereoselective synthesis of 3-substituted 4-(formyloxy)-2-azetidinones by the unusual Baeyer-Villiger reaction of β-lactam aldehydes. Scope and synthetic applications
Alcaide, Benito,Alyt, Moustafa F.,Sierra, Miguel A.
, p. 8819 - 8825 (2007/10/03)
The Baeyer-Villiger oxidation of 4-formyl-β-lactams 1 with m-CPBA gave 4-(formyloxy) β-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) β-lactams 2. Amide or acetoxy substituents at C3 of the four membered ring produce mixtures of 4-(formyloxy) β-lactams 2 and 4-carboxy β-lactams 5. The exclusive formation of carboxy derivatives is observed sometimes for 1-alkyl-substituted-2-azetidinones 1. 4-(Formyloxy) β-lactams 2 are suitable starting materials to prepare different 4-unsubstituted β-lactams 9 using β-hydroxy amides 8 as isolable intermediates. The overall transformation 4-formyl-2-azetidinone to 4-unsubstituted β-lactam is an easy and convenient stereoselective route to these interesting types of compounds.
A study on the asymmetric synthesis of β-lactams through double stereodifferentiating cycloaddition reactions
Palomo, Claudio,Aizpurua, Jesus M.,Mielgo, Antonia,Linden, Anthony
, p. 9186 - 9195 (2007/10/03)
The cycloaddition reaction of chiral aminoketenes, generated from their corresponding acid chlorides and triethylamine, with chiral imines is evaluated as the most direct approach for the construction of cis-β-lactams with the absolute stereochemistry at the C3 and C4 positions being controlled by the ketene partner, independently of the absolute stereochemistry of the imine component.
