Asymmetric Synthesis of 4-Amino-4H-Chromenes by Organocatalytic Oxa-Michael/Aza-Baylis-Hillman Tandem Reactions

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‐4H‐chromenes (see scheme). This reaction takes place in less than 2 h with high yields and excel...

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Bibliographic Details
Published in:Chemistry : a European journal 2010-08, Vol.16 (31), p.9453-9456
Main Authors: Alemán, José, Núñez, Alberto, Marzo, Leyre, Marcos, Vanesa, Alvarado, Cuauhtémoc, García Ruano, José Luis
Format: Article
Language:English
Subjects:
asymmetric synthesis
aza-Baylis-Hillman
Benzopyrans - chemical synthesis
Benzopyrans - chemistry
Catalysis
Chemistry
diarylprolinol ethers
domino reactions
Models, Chemical
Molecular Structure
organocatalysis
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Summary: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‐4H‐chromenes (see scheme). This reaction takes place in less than 2 h with high yields and excellent enantioselectivities.
ISSN:0947-6539
1521-3765
DOI:10.1002/chem.201001293