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Aminocatalytic Strategy for the Synthesis of Optically Active Benzothiophene Derivatives
Author(s) -
Skrzyńska Anna,
Albrecht Anna,
Albrecht Łukasz
Publication year - 2016
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.201600269
Subject(s) - chemistry , benzothiophene , moiety , stereoselectivity , stereocenter , dihydropyran , stereochemistry , pyran , optically active , combinatorial chemistry , organic chemistry , enantioselective synthesis , catalysis , thiophene
A novel approach for the stereoselective synthesis of benzothiophene derivatives with a fused dihydropyran moiety is demonstrated. The reaction of 2‐alkylidenebenzothiophene‐3(2 H )‐ones with dienamines derived from α,β‐unsaturated aldehydes and chiral secondary amines proceeds according to the inverse‐electron‐demand hetero‐Diels–Alder pathway. The formation of the aromatic benzothiophene moiety is a driving force for the developed reaction cascade. Target products bearing three adjacent stereogenic centers are obtained in excellent yields and in a highly stereoselective manner.