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

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

doi:10.1021/acs.orglett.8b02374

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

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

Chemistry and Biochemistry

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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 language	English
Pages (from-to)	6616-6621
Number of pages	6
Journal	Default journal
Volume	20
Issue number	21
DOIs	https://doi.org/10.1021/acs.orglett.8b02374
State	Published - Nov 2 2018

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title = "N-Sulfonyl Bisimidazoline Ligands and Their Applications in Pd(II)-Catalyzed Asymmetric Addition toward alpha-Tertiary Amines",

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.",

author = "Jia-Yin Wang and Meng-Wei Li and Meng-Fan Li and Wen-Juan Hao and Guigen Li and Shu-Jiang Tu and Bo Jiang",

note = "Funding Information: We are grateful for financial support from the NSFC (No 21472071), PAPD of Jiangsu Higher Education Institutions, the Outstanding Youth Fund of JSNU (YQ2015003), and the Robert A. Welch Foundation (D-1361, USA). Publisher Copyright: {\textcopyright} 2018 American Chemical Society.",

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doi = "10.1021/acs.orglett.8b02374",

language = "English",

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T1 - N-Sulfonyl Bisimidazoline Ligands and Their Applications in Pd(II)-Catalyzed Asymmetric Addition toward alpha-Tertiary Amines

AU - Wang, Jia-Yin

AU - Li, Meng-Wei

AU - Li, Meng-Fan

AU - Hao, Wen-Juan

AU - Li, Guigen

AU - Tu, Shu-Jiang

AU - Jiang, Bo

N1 - Funding Information: We are grateful for financial support from the NSFC (No 21472071), PAPD of Jiangsu Higher Education Institutions, the Outstanding Youth Fund of JSNU (YQ2015003), and the Robert A. Welch Foundation (D-1361, USA). Publisher Copyright: © 2018 American Chemical Society.

PY - 2018/11/2

Y1 - 2018/11/2

N2 - 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.

AB - 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.

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U2 - 10.1021/acs.orglett.8b02374

DO - 10.1021/acs.orglett.8b02374

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SN - 1523-7060

VL - 20

SP - 6616

EP - 6621

JO - Default journal

JF - Default journal

IS - 21

ER -

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

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