有機合成化学協会誌
Online ISSN : 1883-6526
Print ISSN : 0037-9980
ISSN-L : 0037-9980
総説および総合論文
トリフルオロメチル基を有するp-キノンメチドを経由した四置換炭素骨格の構築
寺島 究高須賀(川崎) 智子山崎 孝
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2023 年 81 巻 3 号 p. 255-266

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Development of a new synthetic method for the construction of quaternary carbon centers with a trifluoromethyl group was realized by way of smooth 1,6-addition of various active methylene compounds to highly reactive δ-trifluoromethylated p-quinone methides generated in situ only with a catalytic amount of a base. A variety of aldehydes also behaved as nice nucleophiles with the aid of a NHC catalyst and the resultant products were further converted to such congested structures as the consecutive quaternary-tetrasubstituted carbons in a highly stereoselective manner. This method was also extended for the incorporation of heteroatoms like nitrogen, oxygen, and sulfur atoms.

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