Hybrid Diamines Derived from 1,1′-Binaphthyl-2,2′-diamine and α-Amino Acids as Organocatalysts for 1,3-Dipolar Cycloaddition of Aromatic Nitrones to (E)-Crotonaldehyde

Łukasz Weseliński; Paweł Stępniak; Janusz Jurczak; Lukasz Jan Weselinski

doi:10.1055/s-0029-1217808

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Hybrid Diamines Derived from 1,1′-Binaphthyl-2,2′-diamine and α-Amino Acids as Organocatalysts for 1,3-Dipolar Cycloaddition of Aromatic Nitrones to (E)-Crotonaldehyde

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Hybrid Diamines Derived from 1,1′-Binaphthyl-2,2′-diamine and α-Amino Acids as Organocatalysts for 1,3-Dipolar Cycloaddition of Aromatic Nitrones to (E)-Crotonaldehyde

Łukasz Weseliński, Paweł Stępniak, Janusz Jurczak and Lukasz Jan Weselinski

Synlett, Vol.2009(14), pp.2261-2264

01/09/2009

DOI: https://doi.org/10.1055/s-0029-1217808

Abstract

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Abstract Homochiral derivatives of 1,1′-binaphthyl-2,2′-diamine and various α-amino acids were prepared using a convenient procedure. They were tested as organocatalysts for 1,3-dipolar cycloaddition of aromatic nitrones to (E)-crotonaldehyde. The L-phenylalanine-based catalyst 10 afforded superior results, with good ENDO diastereoselectivity, and enantioselectivity of up to 95% ee.

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Title: Hybrid Diamines Derived from 1,1′-Binaphthyl-2,2′-diamine and α-Amino Acids as Organocatalysts for 1,3-Dipolar Cycloaddition of Aromatic Nitrones to (E)-Crotonaldehyde
Creators - without role: Łukasz Weseliński - University of Warsaw
Paweł Stępniak - University of Warsaw
Janusz Jurczak - Institute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, 01-224 Warsaw, Poland, jurczak@icho.edu.pl
Lukasz Jan Weselinski - King Abdullah University of Science & Technology
Publication Details: Synlett, Vol.2009(14), pp.2261-2264
Identifiers: 9943145708331
Academic Unit: King Abdullah University of Science & Technology
Language: English
Resource Type: Journal article