High Performance of a Palladium Phosphinooxazoline Catalyst in the Asymmetric Arylation of Cyclic N-Sulfonyl Ketimines†
Chunhui Jiang
Department of Chemistry, National University of Singapore, 3 Science Drive 3, Singapore 117543 (Singapore)
Search for more papers by this authorCorresponding Author
Prof. Dr. Yixin Lu
Department of Chemistry, National University of Singapore, 3 Science Drive 3, Singapore 117543 (Singapore)
Department of Chemistry, National University of Singapore, 3 Science Drive 3, Singapore 117543 (Singapore)Search for more papers by this authorCorresponding Author
Prof. Dr. Tamio Hayashi
Department of Chemistry, National University of Singapore, 3 Science Drive 3, Singapore 117543 (Singapore)
Institute of Materials Research and Engineering, A*STAR, 3 Research Link, Singapore 117602 (Singapore)
Department of Chemistry, National University of Singapore, 3 Science Drive 3, Singapore 117543 (Singapore)Search for more papers by this authorChunhui Jiang
Department of Chemistry, National University of Singapore, 3 Science Drive 3, Singapore 117543 (Singapore)
Search for more papers by this authorCorresponding Author
Prof. Dr. Yixin Lu
Department of Chemistry, National University of Singapore, 3 Science Drive 3, Singapore 117543 (Singapore)
Department of Chemistry, National University of Singapore, 3 Science Drive 3, Singapore 117543 (Singapore)Search for more papers by this authorCorresponding Author
Prof. Dr. Tamio Hayashi
Department of Chemistry, National University of Singapore, 3 Science Drive 3, Singapore 117543 (Singapore)
Institute of Materials Research and Engineering, A*STAR, 3 Research Link, Singapore 117602 (Singapore)
Department of Chemistry, National University of Singapore, 3 Science Drive 3, Singapore 117543 (Singapore)Search for more papers by this authorWe thank the National University of Singapore and the Ministry of Education (MOE) of Singapore (R-143-000-362-112 and R-143-000-539-133) for financial support.
Graphical Abstract
Chiral cyclic sulfamidates are obtained by the asymmetric addition of arylboronic acids to six-membered cyclic N-sulfonyl ketimines. A cationic palladium complex with a chiral phosphine-oxazoline ligand (iPr-phox) shows high catalytic activity and enantioselectivity to give the products in high yields with 96–99.9 % ee. The cyclic sulfamidates exhibit a tetrasubstituted stereogenic center with an amino group and a triaryl or alkyldiaryl group as substituents.
Abstract
A cationic palladium complex with a chiral phosphine-oxazoline ligand (iPr-phox) showed high catalytic activity and enantioselectivity in the asymmetric addition of arylboronic acids to six-membered cyclic N-sulfonyl ketimines to give high yields of the corresponding chiral cyclic sulfamidates with 96–99.9 % ee. The products have tetrasubstituted stereogenic centers with an amino group and a triaryl or alkyldiaryl group as substituents.
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