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Asymmetric Synthesis of 4‐Amino‐4 H ‐Chromenes by Organocatalytic Oxa‐Michael/Aza‐Baylis–Hillman Tandem Reactions
Author(s) -
Alemán José,
Núñez Alberto,
Marzo Leyre,
Marcos Vanesa,
Alvarado Cuauhtémoc,
García Ruano José Luis
Publication year - 2010
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.201001293
Subject(s) - tandem , chemistry , michael reaction , organocatalysis , baylis–hillman reaction , cascade reaction , stereochemistry , organic chemistry , combinatorial chemistry , enantioselective synthesis , catalysis , materials science , composite material
Quick off the mark! In this work we present the first highly enatioselective oxa‐Michael/aza‐Baylis–Hillman tandem reaction between 2‐alkynals and salicyl N ‐tosylimine leading to optically active 4‐amino‐4 H ‐chromenes (see scheme). This reaction takes place in less than 2 h with high yields and excellent enantioselectivities.