Silicon-Directed Oxa-Pictet−Spengler Cyclization and an Unusual Dimerization of 2-Trimethylsilanyl Tryptophols

Silicon-Directed Oxa-Pictet−Spengler Cyclization and an Unusual Dimerization of 2-Trimethylsilanyl Tryptophols

The tetrahydro-pyrano[3,4-b]indoles 6 were synthesized from 2-(2-trimethylsilanyl-1H-indol-3-yl)-ethanols 5 and various ketones or aldehydes through silicon-directed oxa-Pictet−Spengler cyclizations. An unusual reaction led to the dimeric products 7 when some of 5 was treated with acetone using BF3...

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Veröffentlicht in:Organic letters 2005-05, Vol.7 (10), p.2043-2046
Hauptverfasser: Zhang, Xuqing, Li, Xiaojie, Lanter, James C, Sui, Zhihua
Format: Artikel
Sprache:eng
Schlagworte:
Catalysis
Cyclization
Ethanol - analogs & derivatives
Ethanol - chemistry
Indoles - chemical synthesis
Indoles - chemistry
Molecular Structure
Silicon - chemistry
Trimethylsilyl Compounds - chemistry
Vinyl Compounds - chemical synthesis
Vinyl Compounds - chemistry
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Zusammenfassung:The tetrahydro-pyrano[3,4-b]indoles 6 were synthesized from 2-(2-trimethylsilanyl-1H-indol-3-yl)-ethanols 5 and various ketones or aldehydes through silicon-directed oxa-Pictet−Spengler cyclizations. An unusual reaction led to the dimeric products 7 when some of 5 was treated with acetone using BF3 as the catalyst.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol050623n