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Trans-Selective Conversions of γ-Hydroxy-α,β-Alkynoic Esters to γ-Hydroxy-α,β-Alkenoic Esters

Christopher T. Meta and Kazunori Koide*

*Department of Chemistry, University of Pittsburgh, 219 Parkman Avenue, Pittsburgh, Pennsylvania 15260, Email:

C. T. Meta, K. Koide, Org. Lett., 2004, 6, 1785-1787.

DOI: 10.1021/ol0495366

Conditions a)
Conditions b)


γ-Hydroxy-α,β-acetylenic esters are used as precursors for the preparation of γ-hydroxy-α,β-alkenoic esters by means of trans-selective additions of two hydrogen atoms or one hydrogen atom and one iodine atom across the triple bonds. These methods allow the preparation of β-substituted and α,β-disubstituted alkenoic esters in highly stereoselective manners.

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Key Words

semireduction of alkynes, reduction of unsaturated compounds, Red-Al, sodium borohydride, iodination

ID: J54-Y2004-320