TY - JOUR
T1 - Enantioselective Addition Reaction of Azlactones with Styrene Derivatives Catalyzed by Strong Chiral Brønsted Acids
AU - Kikuchi, Jun
AU - Terada, Masahiro
N1 - Funding Information:
This work was partially supported by a Grant-in-Aid for Scientific Research on Innovative Areas ?Hybrid Catalysis for Enabling Molecular Synthesis on Demand? from MEXT, Japan (No. JP17H06447). We gratefully thank Professor Dr. Cheng, J.-P. (Nankai University) for advice in the theoretical study of the catalyst acidity.
Funding Information:
This work was partially supported by a Grant-in-Aid for Scientific Research on Innovative Areas “Hybrid Catalysis for Enabling Molecular Synthesis on Demand” from MEXT, Japan (No. JP17H06447). We gratefully thank Professor Dr. Cheng, J.-P. (Nankai University) for advice in the theoretical study of the catalyst acidity.
Publisher Copyright:
© 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
PY - 2019/6/17
Y1 - 2019/6/17
N2 - An enantioselective intermolecular addition reaction of azlactones, as carbon nucleophiles, with styrene derivatives, as simple olefins, was demonstrated using a newly developed chiral Brønsted acid catalyst, namely, F10BINOL-derived N-triflyl phosphoramide. Addition products having vicinal tetrasubstituted carbon centers, one of which is an all-carbon quaternary stereogenic center, were formed in good yields with moderate to high stereoselectivities. Extremely high acidity of the new chiral Brønsted acid was confirmed by its calculated pKa value based on DFT studies and is the key to accomplishing not only high catalytic activity but also efficient stereocontrol in the intermolecular addition.
AB - An enantioselective intermolecular addition reaction of azlactones, as carbon nucleophiles, with styrene derivatives, as simple olefins, was demonstrated using a newly developed chiral Brønsted acid catalyst, namely, F10BINOL-derived N-triflyl phosphoramide. Addition products having vicinal tetrasubstituted carbon centers, one of which is an all-carbon quaternary stereogenic center, were formed in good yields with moderate to high stereoselectivities. Extremely high acidity of the new chiral Brønsted acid was confirmed by its calculated pKa value based on DFT studies and is the key to accomplishing not only high catalytic activity but also efficient stereocontrol in the intermolecular addition.
KW - Brønsted acid
KW - acidity
KW - alkenes
KW - asymmetric catalysis
KW - organocatalysis
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U2 - 10.1002/anie.201903111
DO - 10.1002/anie.201903111
M3 - Article
C2 - 31016828
AN - SCOPUS:85065672392
VL - 58
SP - 8458
EP - 8462
JO - Angewandte Chemie - International Edition
JF - Angewandte Chemie - International Edition
SN - 1433-7851
IS - 25
ER -