Premium
Atropisomeric Chiral Dienes in Asymmetric Catalysis: C 2 ‐Symmetric ( Z , Z )‐2,3‐Bis[1‐(diphenylphosphinyl)ethylidene]tetralin as a Highly Active Lewis Base Organocatalyst
Author(s) -
Ogasawara Masamichi,
Kotani Shunsuke,
Nakajima Hikaru,
Furusho Haruka,
Miyasaka Mitsuru,
Shimoda Yasushi,
Wu WeiYi,
Sugiura Masaharu,
Takahashi Tamotsu,
Nakajima Makoto
Publication year - 2013
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201308112
Subject(s) - tetralin , chemistry , lewis acids and bases , catalysis , enantiomer , derivative (finance) , stereochemistry , optically active , twist , frustrated lewis pair , base (topology) , chirality (physics) , medicinal chemistry , organic chemistry , chiral symmetry breaking , physics , symmetry breaking , nambu–jona lasinio model , geometry , mathematics , quantum mechanics , financial economics , economics , mathematical analysis
Diene catalysts with a twist : The title C 2 ‐symmetric tetralin‐fused 1,3‐butadiene derivative is atropisomeric and can be resolved into the two helical enantiomers. The optically pure compound showed excellent enantioselectivity as well as unusually high catalytic activity as a chiral Lewis basic organocatalyst in the asymmetric allylation of various aldehydes with β‐substituted allyltrichlorosilanes (see scheme).