Regiodivergent Asymmetric Conjugate Addition of 2-Furfuryl Ketones to Nitroalkenes Using Thiourea Organocatalysts

Taro Koda; Hiroshi Akutsu; Mitsuaki Suzuki; Kosuke Nakashima; Shin-ichi Hirashima; Akihiro Yoshida; Tsuyoshi Miura; Takashi Yamanoi

doi:10.1055/a-2648-9222

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Synlett
DOI: 10.1055/a-2648-9222

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Regiodivergent Asymmetric Conjugate Addition of 2-Furfuryl Ketones to Nitroalkenes Using Thiourea Organocatalysts

Taro Koda

¹Faculty of Pharmacy and Pharmaceutical Sciences, Josai University, Sakado, Japan (Ringgold ID: RIN34771)

,

Hiroshi Akutsu

¹Faculty of Pharmacy and Pharmaceutical Sciences, Josai University, Sakado, Japan (Ringgold ID: RIN34771)

,

Mitsuaki Suzuki

²Faculty of Sciences, Josai University, Sakado, Japan (Ringgold ID: RIN34771)

,

Kosuke Nakashima

³School of Pharmacy, Tokyo University of Pharmacy and Life Sciences, Tokyo, Japan

,

Shin-ichi Hirashima

³School of Pharmacy, Tokyo University of Pharmacy and Life Sciences, Tokyo, Japan

,

Akihiro Yoshida

¹Faculty of Pharmacy and Pharmaceutical Sciences, Josai University, Sakado, Japan (Ringgold ID: RIN34771)

,

Tsuyoshi Miura

³School of Pharmacy, Tokyo University of Pharmacy and Life Sciences, Tokyo, Japan

,

Takashi Yamanoi

¹Faculty of Pharmacy and Pharmaceutical Sciences, Josai University, Sakado, Japan (Ringgold ID: RIN34771)

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We recently reported the asymmetric ε-regioselective conjugate addition of 2-furfuryl ketones to nitroalkenes utilizing a thiourea-pyrrolidine organocatalyst, resulting in good yields and enantioselectivities. In this study, we present a novel approach for the asymmetric α-regioselective conjugate addition of 2-furfuryl ketones to nitroalkenes using a thiourea-tertiary amine organocatalyst, which has not been previously documented. The reactions produced α-regioselective addition products in high yields and with excellent stereoselectivities. Thus, this work marks the first example of regiodivergent asymmetric conjugate addition of 2-furfuryl ketones to nitroalkenes.

Publication History

Received: 02 June 2025

Accepted after revision: 03 July 2025

Accepted Manuscript online:
03 July 2025

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