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Reactions of p ‐Quinols with Aldehydes and Imines: Stereoselective Access to Polyheterobicyclic and Tricyclic Systems
Author(s) -
GarcíaGarcía Carolina,
Redondo María C.,
Ribagorda María,
Carreño M. Carmen
Publication year - 2014
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201403114
Subject(s) - chemistry , bicyclic molecule , dabco , electrophile , tetrahydrofuran , octane , tricyclic , pyridine , stereoselectivity , dichloromethane , catalysis , organic chemistry , stereochemistry , solvent , medicinal chemistry
Dihydrobenzo[1,3]dioxolanones, tetrahydrobenzo[ d ]oxazolones and heterotricyclic derivatives have been stereoselectively synthesized from p ‐quinols upon reaction with aldehydes or benzaldimines under basic catalysis. Reactions occurred in an experimentally simple one‐pot procedure through a domino sequence of two or three reactions. The choice of 4‐(dimethylamino)pyridine (DMAP) or 1,4‐diazabicyclo[2.2.2]octane (DABCO) as catalyst and MeOH, tetrahydrofuran (THF), or dichloromethane as solvent was essential to achieve the synthesis of bicyclic dioxolanes from aldehydes or bicyclic or tricyclic N,O‐aminals from imines. The stereochemical course of these processes is highly dependent on the nature of the electrophiles.