膦催化烯丙酯的β,γ-Umpolung 级联反应：手性四取代立体碳中心的四氢苯并呋喃酮的简便合成。
Phosphine-Catalyzed β,γ-Umpolung Domino Reaction of Allenic Esters: Facile Synthesis of Tetrahydrobenzofuranones Bearing a Chiral Tetrasubstituted Stereogenic Carbon Center.
机构信息
The Institute of Scientific and Industrial Research (ISIR), Osaka University, Mihogaoka, Ibaraki-shi, Osaka 567-0047 (Japan) http://www.sanken.osaka-u.ac.jp/labs/soc/socmain.html.
Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074 Aachen (Germany).
出版信息
Angew Chem Int Ed Engl. 2015 Dec 14;54(51):15511-5. doi: 10.1002/anie.201508022. Epub 2015 Nov 5.
An enantio-, diastereo-, regio-, and chemoselective phosphine-catalyzed β,γ-umpolung domino reaction of allenic esters with dienones has been developed for the first time. The designed sequence, involving oxy-Michael and Rauhut-Currier reactions, produced highly functionalized tetrahydrobenzofuranones, bearing a chiral tetrasubstituted stereogenic center, in up to 96 % ee.
首次发展了一种对映选择性、非对映选择性、区域选择性和化学选择性膦催化烯丙基酯与二烯酮的β,γ-重排级联反应。所设计的序列涉及氧迈克尔加成反应和劳特-库里尔反应，生成了高度官能化的四氢苯并呋喃酮，带有手性四取代的立体中心，对映体过量高达 96%。
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