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Functionally Substituted Vinyl Carbanions Versatile Intermediates in Heterocyclic Synthesis

✍ Scribed by Richard R. Schmidt

Publisher
Wiley (John Wiley & Sons)
Year
2010
Weight
458 KB
Volume
92
Category
Article
ISSN
0037-9646

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✦ Synopsis

Direct C-lithiation of functionally substituted acrylates yields versatile intermediates for syntheses of butenolides, tetronates, a-hydroxytetronates, pyrrolenines, cyclopentenones, oxalacetates and maleic acid derivatives. A wide variety of substituents are compatible with this lithiation: alkyl, aryl, electron-donating and electron-withdrawing substituents in a-or 8-position conducting to interesting regio-and stereoselectivities. The compounds obtained are portions of many natural products. Approaches to the synthesis of aspertetronins, gregatins, ascorbic acids, chlorotricolide, and KDO will be outlined.

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