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Catalytic Asymmetric Inverse‐Electron‐Demand (IED) [4+2] Cycloaddition of Salicylaldimines: Preparation of Optically Active 4‐Aminobenzopyran Derivatives
Author(s) -
Bernardi Luca,
ComesFranchini Mauro,
Fochi Mariafrancesca,
Leo Virginia,
Mazzanti Andrea,
Ricci Alfredo
Publication year - 2010
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201000608
Subject(s) - cycloaddition , chemistry , optically active , salicylaldehyde , catalysis , phosphoric acid , enantioselective synthesis , furan , inverse , electron , combinatorial chemistry , organic chemistry , stereochemistry , schiff base , physics , geometry , mathematics , quantum mechanics
The catalytic asymmetric inverse‐electron‐demand (IED) [4+2] cycloaddition of various salicylaldehyde‐derived N ‐arylimines with electron‐rich alkenes in the presence of chiral BINOL‐derived phosphoric acid catalysts has been studied with the aim of obtaining optically active 4‐aminobenzopyran derivatives. Dienophiles such as 2,3‐dihydro‐2 H ‐furan, benzyl N ‐vinylcarbamate and 2‐vinylindole have been employed.