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Conformational and electronic preferences in rhodium(II) carboxylate and rhodium(II) carboxamide catalyzed carbon-hydrogen insertion reactions of N,N-disubstituted diazoacetoacetamides

✍ Scribed by Michael P. Doyle; Jack Taunton; Hoan Q. Pho

Publisher: Elsevier Science
Year: 1989
Tongue: French
Weight: 256 KB
Volume: 30
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(01)80577-3

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✦ Synopsis

Conformational preferences dominate electronic influences in governing regioselectivity for catalytic C-H insertion reactions of diazoacetoacetamides and allow the construction of fl-lactams by insertion a and f3 to an ester functional group.

We have recently reported a new methodology for the synthesis of p-lactam compounds through intramolecular carbon-hydrogen insertion caused by rhodium(ll) acetate catalyzed decomposition of Nbenzyl and N-alkyl diazoacetoacetamides.

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