Dienamine‐Mediated Asymmetric Inverse‐Electron‐Demand Hetero‐Diels–Alder Reaction of Linear Deconjugated Enones: Diversity‐Oriented Synthesis of 3,4‐Dihydropyrans | Zendy

Maity Rajendra | Zendy; Pan Subhas Chandra | Zendy

Premium

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.

This content is not available in your region!

Continue researching here.

Having issues? You can contact us here

Accelerating Research