Phosphine-Catalyzed [beta],[gamma]-Umpolung Domino Reaction of Allenic Esters: Facile Synthesis of Tetrahydrobenzofuranones Bearing a Chiral Tetrasubstituted Stereogenic Carbon Center

An enantio-, diastereo-, regio-, and chemoselective phosphine-catalyzed [beta],[gamma]-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 tetrahydrob...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2015-12, Vol.54 (51), p.15511
Main Authors: Takizawa, Shinobu, Kishi, Kenta, Yoshida, Yasushi, Mader, Steffen, Arteaga, Fernando Arteaga, Lee, Shoukou, Hoshino, Manabu, Rueping, Magnus, Fujita, Makoto, Sasai, Hiroaki
Format: Article
Language:English
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Summary:An enantio-, diastereo-, regio-, and chemoselective phosphine-catalyzed [beta],[gamma]-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.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201508022