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Stereoselective Azepine-Ring Formation Through Ene Reactions of 3-(Alk-2-enyl)amino-2-cyanoacrolein Derivatives

✍ Scribed by Michihiko Noguchi; Hisashi Yamada; Shinji Takamura; Takehiko Uchida; Mitsuko Hironaka; Akikazu Kakehi; Hidetoshi Yamamoto

Publisher: John Wiley and Sons
Year: 2000
Tongue: English
Weight: 346 KB
Volume: 2000
Category: Article
ISSN: 1434-193X
DOI: 10.1002/(sici)1099-0690(200004)2000:8<1489::aid-ejoc1489>3.0.co;2-z

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✦ Synopsis

Ene reactions / Azepines / 3-(Alk-2-enyl)aminoacroleins

The reaction of 3-[N-(alk-2-enyl)benzylamino]-2-cyanoacroleins 9 with primary amines 12 and 13 gave 4,5-dihydro-1Hazepines 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 Scheme 1

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