Dynamic Kinetic Resolution in the Asymmetric Synthesis of β‐Amino Acids by Organocatalytic Reduction of Enamines with Trichlorosilane | Zendy

Malkov Andrei V. | Zendy; Stončius Sigitas | Zendy; Vranková Kvetoslava | Zendy; Arndt Matthias | Zendy; Kočovský Pavel | Zendy

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Dynamic Kinetic Resolution in the Asymmetric Synthesis of β‐Amino Acids by Organocatalytic Reduction of Enamines with Trichlorosilane

Author(s) -

Malkov Andrei V.,

Stončius Sigitas,

Vranková Kvetoslava,

Arndt Matthias,

Kočovský Pavel

Publication year - 2008

Publication title -

chemistry – a european journal

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.687

H-Index - 242

eISSN - 1521-3765

pISSN - 0947-6539

DOI - 10.1002/chem.200801244

Subject(s) - enamine , chemistry , imine , trichlorosilane , valine , organocatalysis , reduction (mathematics) , amino acid , catalysis , combinatorial chemistry , enantioselective synthesis , organic chemistry , biochemistry , mathematics , geometry , silicon

Resolved dynamically : A new, expedient protocol has been developed for the asymmetric synthesis of β 3 ‐ and β 2, 3 ‐amino acid derivatives from enamine precursors (see scheme). The method relies on a fast equilibrium between the enamine and imine forms. Reduction of the imine with Cl 3 SiH, catalyzed by the L ‐valine‐derived formamide L* (5 mol %), afforded the corresponding amino esters in good yields, good enantioselectivities (≤90 % ee ) and high diastereoselectivities (≤99 % de ).

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