Phosphine-Catalyzed β,γ-Umpolung Domino Reaction of Allenic Esters: Facile Synthesis of Tetrahydrobenzofuranones Bearing a Chiral Tetrasubstituted Stereogenic Carbon Center.
Journal: Angewandte Chemie (International Ed. In English)
Published:
Abstract
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.
Authors
Shinobu Takizawa, Kenta Kishi, Yasushi Yoshida, Steffen Mader, Fernando Arteaga, Shoukou Lee, Manabu Hoshino, Magnus Rueping, Makoto Fujita, Hiroaki Sasai