Phosphine-Catalyzed β,γ-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 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 tetrahydrobenzofuranon...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2015-12, Vol.54 (51), p.15511-15515
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
Subjects:
allenes
annulations
Cascade chemical reactions
Esters
organocatalysis
Phosphine
Phosphines
umpolung
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Summary: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. Domino effect: 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.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201508022