Organocatalysis with Chiral Formamides: Asymmetric Allylation and Reduction of Imines | Zendy

Baudequin Christine | Zendy; Chaturvedi Devdutt | Zendy; Tsogoeva Svetlana B. | Zendy

AI Assistant Blog Pricing

Home ZAIA Blog

Premium

Organocatalysis with Chiral Formamides: Asymmetric Allylation and Reduction of Imines

Author(s) -

Baudequin Christine,

Chaturvedi Devdutt,

Tsogoeva Svetlana B.

Publication year - 2007

Publication title -

european journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.825

H-Index - 155

eISSN - 1099-0690

pISSN - 1434-193X

DOI - 10.1002/ejoc.200700058

Subject(s) - chemistry , formamides , enantioselective synthesis , aldimine , organocatalysis , amine gas treating , formamide , yield (engineering) , medicinal chemistry , moiety , catalysis , organic chemistry , materials science , metallurgy

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 C 2 ‐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 ). (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)

This content is not available in your region!

Continue researching here.

Having issues? You can contact us here

Accelerating Research