2020年7月2日
Brønsted Base-Catalyzed Transformation of α,β-Epoxyketones Utilizing [1,2]-Phospha-Brook Rearrangement for the Synthesis of Allylic Alcohols Having a Tetrasubstituted Alkene Moiety
Organic Letters
- ,
- ,
- ,
- 巻
- 22
- 号
- 13
- 開始ページ
- 5170
- 終了ページ
- 5175
- 記述言語
- 英語
- 掲載種別
- 研究論文(学術雑誌)
- DOI
- 10.1021/acs.orglett.0c01765
- 出版者・発行元
- American Chemical Society ({ACS})
A stereoselective transformation of α,β-epoxyketones into alkenylphosphates having a hydroxymethyl group on the β-carbon was established by utilizing the [1,2]-phospha-Brook rearrangement under Brønsted base catalysis. The reaction involves the catalytic generation of an α-oxygenated carbanion located at the α-position of an epoxide moiety through the [1,2]-phospha-Brook rearrangement and the following epoxide opening. Further transformation of the alkenylphosphates by the palladium-catalyzed cross-coupling reaction with Grignard reagents provided allylic alcohols having a stereodefined all-carbon tetrasubstituted alkene moiety.
- リンク情報
- ID情報
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- DOI : 10.1021/acs.orglett.0c01765
- ISSN : 1523-7060
- eISSN : 1523-7052
- ORCIDのPut Code : 75794344
- PubMed ID : 32610917
- SCOPUS ID : 85087116603