Enantiopure P-Chiral Secondary Phosphines (P*HRR′) from the Catalytic Asymmetric Hydrogenation of P═C Bonds,Journal of the American Chemical Society

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Enantiopure P-Chiral Secondary Phosphines (P*HRR′) from the Catalytic Asymmetric Hydrogenation of P═C Bonds
Journal of the American Chemical Society ( IF 14.4 ) Pub Date : 2024-09-13 , DOI: 10.1021/jacs.4c09501
Ming Li ₁ , Aaron A Mitchell ₁ , Tian Zhang ₁ , Brian O Patrick ₁ , Michael D Fryzuk ₁ , Derek P Gates ₁

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We report the first bottleable enantiopure P-chiral secondary phosphines from the rhodium-catalyzed asymmetric hydrogenation of phosphaalkenes. Catalytic asymmetric hydrogenation, a reaction of broad academic and industrial importance for C═C, N═C, and O═C bonds, has not previously been reported for the P═C bond. The hydrogenation of ArP═CR₂ (Ar = Mes, m-Xyl and TMOP; R = Ph, 4-C₆H₄F) affords four unprecedented P-stereogenic secondary phosphines in 76%–90% isolated yields with 91%–97% enantiomeric excess (ee). These isolable P-chiral secondary phosphines are configurationally stable indefinitely in the solid state and show only modest loss in ee when kept in solution for over a month at room temperature.

中文翻译：

P=C 键催化不对称氢化反应生成对映体纯 P-手性仲膦 (P*HRR′)

我们报道了第一个可瓶装的对映体纯P-手性仲膦，其由铑催化的磷烯烃不对称氢化反应产生。催化不对称氢化是一种对 C=C、N=C 和 O=C 键具有广泛学术和工业重要性的反应，此前尚未报道过 P=C 键的催化不对称氢化反应。 ArP=CR ₂ （Ar = Mes、 m -Xyl 和 TMOP；R = Ph、4-C ₆ H ₄ F）的氢化提供了四种前所未有的P -立体仲膦，分离产率为 76%–90%，分离产率为 91%– 97% 对映体过量 (ee)。这些可分离的P-手性仲膦在固态下构型无限稳定，并且当在室温下在溶液中保存一个多月时，ee 仅表现出适度的损失。

更新日期：2024-09-13

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