2005年3月
5-Exo versus 6-endo cyclization of nucleoside 2-sila-5-hexenyl radicals: Reaction of 6-(bromomethyl)dimethylsilyl 1 ',2 '-unsaturated uridines
JOURNAL OF ORGANIC CHEMISTRY
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- 巻
- 70
- 号
- 5
- 開始ページ
- 1684
- 終了ページ
- 1690
- 記述言語
- 英語
- 掲載種別
- 研究論文(学術雑誌)
- DOI
- 10.1021/jo040260p
- 出版者・発行元
- AMER CHEMICAL SOC
The mode of cyclization of 2-sila-5-hexen-1-yl radicals generated from 6-(bromomethyl)dimethylsilyl-1',2'-unsaturated uridines was investigated. In contrast to the case of the 2'-unsubstituted 6-silicontethered substrate (4), which undergoes exclusive 6-endo-cyclization, reactions of the 2'-substituted (Me, CO2Me, OBz, and Cl) derivatives (14, 20, 22, and 24) uniformly proceeded in preferential or exclusive 5-exo-mode. The Tamao oxidation of the resulting cyclized products was also carried out to synthesize the corresponding 1'-C-hydroxymethyl derivatives.
- リンク情報
- ID情報
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- DOI : 10.1021/jo040260p
- ISSN : 0022-3263
- Web of Science ID : WOS:000227246800021