N-Sulfonyl Bisimidazoline Ligands and Their Applications in Pd(II)-Catalyzed Asymmetric Addition toward α-Tertiary Amines

Jia Yin Wang, Meng Wei Li, Meng Fan Li, Wen Juan Hao, Guigen Li, Shu Jiang Tu, Bo Jiang

Research output: Contribution to journalArticle

8 Scopus citations

Abstract

A new class of chiral N-sulfonyl bisimidazoline (Bim) ligands have been designed, prepared, and applied in Pd(II)-catalyzed asymmetric addition of arylboronic acids to isatin-derived N-Boc ketimines. The combination of Pd(OCOCF 3 ) 2 and N-tosyl Bim ligand shows high catalytic activity and excellent asymmetric induction, enabling asymmetric addition to offer α-tertiary amines with generally good to high yields and excellent enantioselectivity (up to 96% yield, 96% ee). This asymmetric Pd(II) catalysis can tolerate air conditions, providing a practical and operationally simple protocol toward the construction of an enantioenriched α-tertiary stereocenter.

Original languageEnglish
Pages (from-to)6616-6621
Number of pages6
JournalOrganic Letters
Volume20
Issue number21
DOIs
StatePublished - Nov 2 2018

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