A stereoselective synthesis of 1-phenyl-1-buten-3-yne and some 1-heteroaryl analogues.

Marco Fossatelli, Anca C.T.H.M. van der Kerk, Sergei F. Vasilevsky, Lambert Brandsma

Результат исследования: Материалы для журналаСтатья

6 Цитирования (Scopus)

Аннотация

Z-Enynes, RCHCHCCH (R= phenyl, 2-furyl, 2- and 3-thienyl and 3-pyridyl) can be obtained in ∼ 40% overall yields and with a stereoselectivity of > 95% by Pd/Cu-catalyzed cross-coupling of the readily available enyne sulfide HCCCHCHSC2H5 with RBr and RI, reduction of the products with activated zinc powder in ethanol and elimination of ethanethiol from the reduction products RCHCHCHCHSC2H5 with an excess of sodamide in liquid ammonia. In the case of the 2-pyridyl-substituted substrate the E-enyne HCCCHCH-2-pyridyl is isolated.

Язык оригиналаАнглийский
Страницы (с... по...)4229-4232
Количество страниц4
ЖурналTetrahedron Letters
Том33
Номер выпуска29
DOI
Статус публикацииОпубликовано - 14 июл 1992
Опубликовано для внешнего пользованияДа

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ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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