ヨシゴエ　ユウスケ   吉越　裕介    所属   千葉工業大学  工学部 教育センター（工学部）    職種   准教授
言語種別	英語
発行・発表の年月	2021/12
形態種別	学術雑誌
査読	査読あり
標題	The Aza-Prins Reaction of 1,2-Dicarbonyl Compounds with 3-Vinyltetrahydroquinolines: Application to the Synthesis of Polycyclic Spirooxindole Derivatives.
執筆形態	共著
掲載誌名	The Journal of organic chemistry
掲載区分	国外
巻・号・頁	86(23),pp.16425-16433
著者・共著者	Shinichi Saito, Tomohiro Katamura, Rei Tsukazaki, Akito Fujisawa, Yusuke Yoshigoe, Yuichiro Mutoh
概要	The aza-Prins reaction of 6,7-dimethoxy-3-vinyl-1,2,3,4-tetrahydroquinoline (1) with 1,2-dicarbonyl compounds proceeded smoothly in the presence of HCl, and the corresponding tricyclic benzazocines were isolated in yields of 20-86%. The reaction proceeded in a stereoselective manner, and the formation of the 2,4-trans isomer was observed. The reaction of 1 with an enantiopure ketoester gave the corresponding tricyclic benzazocine as a mixture of diastereomers. The diastereomers were easily separated and converted to enantiopure tricyclic benzazocines. The synthesis of spirooxindole derivatives was achieved by the reaction of 1 with isatin derivatives.
DOI	10.1021/acs.joc.1c01785
ISSN	1520-6904
PMID	34792347