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The nucleophilic addition of ethyl 3-propionylzinc iodide to a variety of differently protected pentopyranose derived d-glycals 6a-g proceeds with good to high levels of diastereoselectivity to provide the corresponding β-C-glycosides 7. The stereochemistry of the para-nitrobenzoate derivative 7d has been confirmed by X-ray crystallography, and the stereochemistry of the other β-C-glycoside products...
Using azomethine ylid reactivity available from the β-lactam-based oxazolidinone 1, selenoketones 6a-e react as 1,3-dipolarophiles to give racemic selenapenams 7a-e in a single step. The cycloaddition sequence proceeds with complete control of regiochemistry and the thermodynamically more stable C(3)/C(5) relationship is observed. The selenothiocarboxylate 9a and the selenocarboxylate 9b also function...
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