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Organocatalysis with Chiral Formamides: Asymmetric Allylation and Reduction of Imines

Abstract : Simple aldimine, derived from p‐nitrobenzaldehyde and 2‐aminophenol, reacts with allyltrichlorosilane in the presence of chiral N‐formylproline activator 5 and an L‐proline additive to afford the corresponding homoallylic amine in good yield (84 %) and with moderate enantioselectivity (43 % ee). The role of the second formamide moiety in the activator is crucial to bring about the enhancement in the reaction rate and enantioselectivity, as C2‐chiral bisformamide 1 promotes for the same allylation reaction in higher yield (94 %) and enantioselectivity (83 % ee). Chiral monoformamide 5 (10 mol‐%), with the assistance of HMPA as an additive, also catalyses the asymmetric reduction of ketimine 13 in the presence of trichlorosilane in good yield and enantioselectivity (75 %, 81 % ee).
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https://hal-normandie-univ.archives-ouvertes.fr/hal-02385359
Contributor : Christine Baudequin <>
Submitted on : Thursday, November 28, 2019 - 5:28:08 PM
Last modification on : Thursday, July 2, 2020 - 3:28:45 AM

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Christine Baudequin, Devdutt Chaturvedi, Svetlana Tsogoeva. Organocatalysis with Chiral Formamides: Asymmetric Allylation and Reduction of Imines. European Journal of Organic Chemistry, Wiley-VCH Verlag, 2007, 2007 (16), pp.2623-2629. ⟨10.1002/ejoc.200700058⟩. ⟨hal-02385359⟩

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