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Dienamine‐Mediated Asymmetric Inverse‐Electron‐Demand Hetero‐Diels–Alder Reaction of Linear Deconjugated Enones: Diversity‐Oriented Synthesis of 3,4‐Dihydropyrans
Author(s) -
Maity Rajendra,
Pan Subhas Chandra
Publication year - 2017
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.201601575
Subject(s) - chemistry , stereocenter , dihydropyran , organocatalysis , enantioselective synthesis , catalysis , diels–alder reaction , amine gas treating , organic chemistry , stereochemistry
The first organocatalytic asymmetric inverse‐electron‐demand Diels–Alder reaction of deconjugated enones by using a linear dienamine was explored. Electron‐poor oxadienes having a cyano group were found to be suitable in this reaction. With a 20 mol‐% loading of a quinine‐derived primary amine catalyst, high yields and excellent enantioselectivities were attained for a variety of 2,4‐stereogenic 3,4‐dihydropyran products under mild reaction conditions.