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Practical Asymmetric Synthesis of Chiral Sulfoximines via Sulfur-Selective Alkylation

Yoshiaki Maeda, Suguru Hamada, Yusuke Aota, Kazuya Otsubo, Taichi Kano* and Keiji Maruoka*

*Tokyo University of Agriculture and Technology, Koganei, Tokyo 184-8588; Kyoto University, Sakyo, Kyoto 606-8501, Japan, Email: kanogo.tuat.ac.jp, maruoka.keiji.4wkyoto-u.ac.jp

Y. Maeda, S. Hamada, Y. Aota, K. Otsubo, T. Kano, K. Maruoka, J. Org. Chem., 2022, 87, 3652-3660.

DOI: 10.1021/acs.joc.1c02424


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Abstract

Chiral sulfoximines are promising bioisosteres in medicinal chemistry. A stereospecific S-alkylation of readily accessible chiral sulfinamides enables an asymmetric synthesis of chiral sulfoximines under practical conditions.

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De-tert-butylation of a Sulfoximine and Subsequent S-Alkylation



Asymmetric Synthesis of Chiral Sulfoximines via the S-Arylation of Sulfinamides

Y. Aota, T. Kano, K. Maruoka, J. Am. Chem. Soc., 2019, 141, 19263-19268.


Key Words

sulfoximines


ID: J42-Y2022