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Paper | Special issue | Vol 103, No. 2, 2021, pp.839-861
Published online, 1st March, 2021
DOI: 10.3987/COM-20-S(K)52
A Fluorous Proline Catalyst Immobilized on Teflon® for Highly Stereoselective Asymmetric Aldol Reactions

Kazuki Ishihara, Riho Obayashi, Mizuki Ohira, Yuki Kobayashi, Kotaro Ishihara, Yamato Kato, Narisa Takeuchi, Risa Mizuno, Takayuki Shioiri, and Masato Matsugi*

*Faculty of Agriculture, Meijo University, 1-501 Shiogamaguchi, Tempaku-ku, Nagoya 468-8502, Japan

Abstract

An immobilized fluorous-tagged proline catalyst and its application as a recycling system in highly stereoselective asymmetric aldol reactions is described. The introduction of acidic sulfonamide groups bearing multifluorous tags at the carboxy position proved to be more effective than the introduction of bulky substituents on the proline backbone to achieve high stereoselectivity. The Teflon®-immobilized proline catalyst could be recovered and reused at least five times while maintaining high levels of catalytic activity and stereoselectivity.