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

Research output: Contribution to journalArticle

6 Citations (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)4229-4232
Number of pages4
JournalTetrahedron Letters
Volume33
Issue number29
DOIs
Publication statusPublished - 14 Jul 1992
Externally publishedYes

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Sulfides
Ammonia
Powders
Zinc
Ethanol
Stereoselectivity
Liquids
Substrates
ethanethiol

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

A stereoselective synthesis of 1-phenyl-1-buten-3-yne and some 1-heteroaryl analogues. / Fossatelli, Marco; van der Kerk, Anca C.T.H.M.; Vasilevsky, Sergei F.; Brandsma, Lambert.

In: Tetrahedron Letters, Vol. 33, No. 29, 14.07.1992, p. 4229-4232.

Research output: Contribution to journalArticle

Fossatelli, Marco ; van der Kerk, Anca C.T.H.M. ; Vasilevsky, Sergei F. ; Brandsma, Lambert. / A stereoselective synthesis of 1-phenyl-1-buten-3-yne and some 1-heteroaryl analogues. In: Tetrahedron Letters. 1992 ; Vol. 33, No. 29. pp. 4229-4232.
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