title: Phosphine-Catalyzed β,γ-Umpolung Domino Reaction of Allenic Esters: Facile Synthesis of Tetrahydrobenzofuranones Bearing a Chiral Tetrasubstituted Stereogenic Carbon Center.
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.affiliation: 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.
authors.forename: Shinobu
authors.initials: S
authors.lastname: Takizawa
authors.affiliation: 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.
authors.forename: Kenta
authors.initials: K
authors.lastname: Kishi
authors.affiliation: 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.
authors.forename: Yasushi
authors.initials: Y
authors.lastname: Yoshida
authors.affiliation: Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074 Aachen (Germany).
authors.forename: Steffen
authors.initials: S
authors.lastname: Mader
authors.affiliation: 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.
authors.forename: Fernando Arteaga
authors.initials: FA
authors.lastname: Arteaga
authors.affiliation: Department of Applied Chemistry, School of Engineering, The University of Tokyo, Tokyo 113-8656 (Japan).
authors.forename: Shoukou
authors.initials: S
authors.lastname: Lee
authors.affiliation: Department of Applied Chemistry, School of Engineering, The University of Tokyo, Tokyo 113-8656 (Japan).
authors.forename: Manabu
authors.initials: M
authors.lastname: Hoshino
authors.affiliation: Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074 Aachen (Germany).
authors.forename: Magnus
authors.initials: M
authors.lastname: Rueping
authors.affiliation: Department of Applied Chemistry, School of Engineering, The University of Tokyo, Tokyo 113-8656 (Japan).
authors.forename: Makoto
authors.initials: M
authors.lastname: Fujita
authors.affiliation: 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. sasai@sanken.osaka-u.ac.jp.
authors.forename: Hiroaki
authors.initials: H
authors.lastname: Sasai
keywords: allenes; annulations; organocatalysis; phosphines; umpolung