1,2,3‐Trisubstituted donor–acceptor cyclopropenes (DACPs) generated in situ from enoldiazo compounds react with nucleophiles to form α‐substituted succinic acid derivatives in high yields. Initial dirhodium(II) carboxylate catalysis rapidly converts enoldiazo‐acetates or ‐acetamides to DACPs that undergo catalyst‐free Favorskii ring opening with amines, and also with anilines, alcohols, and thiols, when facilitated by catalytic amounts of 4‐dimethylaminopyridine (DMAP). This methodology provides easy access to mixed esters and amides of monosubstituted succinic acids, including derivatives of naturally occurring compounds. It also affords dihydrazide, dihydroxamic acid, and diamide derivatives, as well as α‐substituted tetrahydropyridazine‐3,6‐diones in high yields. Attempts to generate optically enriched DACPs were not successful because their populations having the
- Award ID(s):
- 1709564
- NSF-PAR ID:
- 10195404
- Date Published:
- Journal Name:
- Molecules
- Volume:
- 25
- Issue:
- 19
- ISSN:
- 1420-3049
- Page Range / eLocation ID:
- 4477
- Format(s):
- Medium: X
- Sponsoring Org:
- National Science Foundation
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