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Stereoselective Azepine‐Ring Formation Through Ene Reactions of 3‐(Alk‐2‐enyl)amino‐2‐cyanoacrolein Derivatives
Author(s) -
Noguchi Michihiko,
Yamada Hisashi,
Takamura Shinji,
Uchida Takehiko,
Hironaka Mitsuko,
Kakehi Akikazu,
Yamamoto Hidetoshi
Publication year - 2000
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/(sici)1099-0690(200004)2000:8<1489::aid-ejoc1489>3.0.co;2-z
Subject(s) - azepine , chemistry , ene reaction , stereoselectivity , intramolecular force , ring (chemistry) , imine , olefin fiber , stereochemistry , medicinal chemistry , organic chemistry , catalysis
The reaction of 3‐[ N ‐(alk‐2‐enyl)benzylamino]‐2‐cyanoacroleins 9 with primary amines 12 and 13 gave 4,5‐dihydro‐1 H ‐azepines 14 and 15 stereoselectively, through an intramolecular ene reaction of the imine derivatives of 9 . Similarly, carbonyl‐ene reaction of acrolein derivatives 9 , and olefin‐ene reaction of their conjugated diene compounds 22 , and 24 ‐ 27 are also discussed. These ene reactions established an efficient synthetic approach toward monocyclic azepine ring formation.