Enantioselective Synthesis of Polycyclic Nitrogen Heterocycles by Rh-Catalyzed Alkene Hydroacylation: Constructing Six-Membered Rings in the Absence of Chelation Assistance

Catalytic, enantioselective hydroacylations of N-allylindole-2-carboxaldehydes and N-allylpyrrole-2-carboxaldehydes are reported. In contrast to many alkene hydroacylations that form six-membered rings, these annulative processes occur in the absence of ancillary functionality to stabilize the acy...

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Veröffentlicht in:	Organic letters 2014-08, Vol.16 (15), p.4036-4039
Hauptverfasser:	Du, Xiang-Wei, Ghosh, Avipsa, Stanley, Levi M
Format:	Artikel
Sprache:	eng
Schlagworte:	Aldehydes - chemistry Alkenes - chemistry Catalysis Chelating Agents - chemistry chelation chemical structure enantioselective synthesis enantioselectivity Heterocyclic Compounds - chemical synthesis Heterocyclic Compounds - chemistry hydrides Ketones - chemical synthesis Ketones - chemistry Letter Molecular Structure nitrogen Nitrogen - chemistry organic compounds Rhodium - chemistry Stereoisomerism
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Beschreibung
Zusammenfassung:	Catalytic, enantioselective hydroacylations of N-allylindole-2-carboxaldehydes and N-allylpyrrole-2-carboxaldehydes are reported. In contrast to many alkene hydroacylations that form six-membered rings, these annulative processes occur in the absence of ancillary functionality to stabilize the acylrhodium(III) hydride intermediate. The intramolecular hydroacylation reactions generate 7,8-dihydropyrido[1,2-a]indol-9(6H)ones and 6,7-dihydroindolizin-8(5H)-ones in moderate to high yields with excellent enantioselectivities.
ISSN:	1523-7060 1523-7052 1523-7052
DOI:	10.1021/ol501869s