TY - JOUR
T1 - Phosphine-Catalyzed β,γ-Umpolung Domino Reaction of Allenic Esters
T2 - Facile Synthesis of Tetrahydrobenzofuranones Bearing a Chiral Tetrasubstituted Stereogenic Carbon Center
AU - Takizawa, Shinobu
AU - Kishi, Kenta
AU - Yoshida, Yasushi
AU - Mader, Steffen
AU - Arteaga, Fernando Arteaga
AU - Lee, Shoukou
AU - Hoshino, Manabu
AU - Rueping, Magnus
AU - Fujita, Makoto
AU - Sasai, Hiroaki
N1 - Funding Information:
This study was supported by a Grant-in-Aid for Scientific Research on Innovative Areas-Advanced Molecular Transformations by Organocatalysis-from The Ministry of Education, Culture, Sports, Science and Technology (MEXT), Japan, the CREST project of the Japan Science and Technology Corporation (JST), and JST Advance Catalytic Transformation Program for Carbon Utilization (ACT-C). We thank the Deutsche Forschungsgemeinschaft (scholarship for S.M., International Research Training Group "Selectivity in Chemo- and Biocatalysis", SeleCa, Germany) and the JSPS Japanese-German Graduate Externship. We acknowledge the technical staff of the Comprehensive Analysis Center of ISIR, Osaka University (Japan).
Publisher Copyright:
© 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
PY - 2015/12/14
Y1 - 2015/12/14
N2 - 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.
AB - 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.
KW - allenes
KW - annulations
KW - organocatalysis
KW - phosphines
KW - umpolung
UR - http://www.scopus.com/inward/record.url?scp=84955193973&partnerID=8YFLogxK
U2 - 10.1002/anie.201508022
DO - 10.1002/anie.201508022
M3 - Article
C2 - 26537173
AN - SCOPUS:84955193973
SN - 1433-7851
VL - 54
SP - 15511
EP - 15515
JO - Angewandte Chemie - International Edition
JF - Angewandte Chemie - International Edition
IS - 51
ER -