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ChemInform Abstract: New Synthesis of Fused Tricyclic 2-Azetidinones Using Stereoselective Allylation of cis-4-Formyl-β-lactams and Intramolecular Diels—Alder Reaction.

✍ Scribed by Benito Alcaide; Pedro Almendros

Publisher
John Wiley and Sons
Year
2010
Weight
35 KB
Volume
30
Category
Article
ISSN
0931-7597

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✦ Synopsis

New Synthesis of Fused Tricyclic 2-Azetidinones Using Stereoselective Allylation of cis-4-Formyl-β-lactams and Intramolecular Diels-Alder Reaction.

-SnCl 4 -promoted addition of (II) to azetidinones (I) gives 1-hydroxy-homoallyl-β-lactams (III) with excellent stereoselectivities.

The mesylates of alcohols (V) are used for the diastereoselective preparation of both 4-butadienylazetidinones (VI) and fused tricyclic β-lactams through a tandem one-pot elimination-intramolecular Diels-Alder reaction.

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ChemInform Abstract: Stereoselective Synthesis of New β-Lactams by Cyclocondensation of 1-Methoxy-3-(trimethylsilyloxy)-1,3-butadiene with 4-Formyl Substituted Azetidinones.
✍ Rita Annunziata; Maurizio Benaglia; Mauro Cinquini; Franco Cozzi; Fernando Monta 📂 Article 📅 2010 🏛 John Wiley and Sons ⚖ 32 KB

Stereoselective Synthesis of New β-Lactams by Cyclocondensation of 1-Methoxy-3-(trimethylsilyloxy)-1,3-butadiene with 4-Formyl Substituted Azetidinones. -Lewis acid promoted hetero Diels-Alder reaction of Danishefsky's diene (II) with enantiomerically pure azetidin-2-one derivatives (I) affords pre