期刊
ADVANCED SYNTHESIS & CATALYSIS
卷 353, 期 4, 页码 585-594出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.201100049
关键词
alkynes; allenes; iron; pyrroles; rearrangement
资金
- DGI-MICINN [CTQ2009-09318]
- Comunidad Autonoma de Madrid [S2009/PPQ-1752]
- UCM-BSCH [GR58/08]
- MEC
2-Azetidinone-tethered alkynols and allenols, readily prepared from a propanylidene beta-lactam aldehyde, were used as starting materials for divergent ring expansion reactions catalyzed by iron(III) chloride. Worthy of note, in contrast to the iron-catalyzed reactions of beta-lactam allenols which lead to gamma-lactones, the reaction of beta-lactam alkynols under identical conditions gives pyrroles. The gold-catalyzed 6-endo aminocyclization of these allenic gamma-lactones formed fused dihydropyridines. The iron-catalyzed formation of pyrroles may proceed through a Meyer-Schuster rearrangement followed by beta-lactam ring opening and cyclization by attack of the amino group to the ketone.
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