The extended Corey-Chaykovsky reaction: double methylene transfer to activated Knoevenagel adducts

Авторы: Shorokhov V.V., Nikolaeva A.A., Zhokhov S.S., Trushkov I.V., Ivanova O.A.
Сборник: Успехи синтеза и комплексообразования = Advances in synthesis and complexing : сборник тезисов шестой Международной научной конференции
Тезисы
Год издания: 2022
Место издания: РУДН Москва
Первая страница: 123
Последняя страница: 123
Аннотация: In this work we present extended Corey-Chaykovsky reaction as a versatile approach for synthesis of benzylcyclopropanes 2 and their analogs 3 via reaction of the excess of Corey ylide with readily available 4-hydroxyphenyl- and 1H- or 1-p-tosyl 3-indolyl-substituted alkenes 1. This reaction proceeds as double methylene transfer from Corey ylide to activated Knoevenagel adducts. Investigation of mechanism, including studies of deuterium labelled Corey ylide, allowed us to conclude that the presence of electron releasing groups in (het)aryl substituent and ability to ipso attack play a crucial role for the realization of this domino process. Oppositely, common cyclopropanes 4,5 were obtained using substrates bearing 3-nitro- or 4-TsNH groups.
Добавил в систему: Шорохов Виталий Владимирович

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