Highly Efficient Trapping of the Nazarov Intermediate with Substituted Arenes

Highly Efficient Trapping of the Nazarov Intermediate with Substituted Arenes

1,4-Dien-3-ones bearing pendant arylethyl side chains were readily prepared from substituted dihydrocinnamaldehydes. When treated with TiCl4 at low temperature, these compounds underwent domino cyclization to give benzohydrindenones in near-quantitative yield and with complete diastereoselectivity.

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Veröffentlicht in:Organic letters 2001-09, Vol.3 (19), p.3033-3035
Hauptverfasser: Browder, Cindy C, Marmsäter, Fredrik P, West, F. G
Format: Artikel
Sprache:eng
Schlagworte:
Heterocyclic Compounds, 3-Ring - chemical synthesis
Heterocyclic Compounds, 3-Ring - chemistry
Hydrocarbons, Cyclic - chemistry
Stereoisomerism
Titanium - chemistry
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Zusammenfassung:1,4-Dien-3-ones bearing pendant arylethyl side chains were readily prepared from substituted dihydrocinnamaldehydes. When treated with TiCl4 at low temperature, these compounds underwent domino cyclization to give benzohydrindenones in near-quantitative yield and with complete diastereoselectivity.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol010159w