Stereoselective Synthesis of Difunctionalized 1,3-Dienes Containing Silicon and Selenium via Hydrozirconation of (Z)-3-(Trimethylsilyl)alk 3-en-1-ynes

摘要

Sonogashira coupling of (E)-a-iodovinylsilanes 1 with (trimethylsilyl)acetylene gave (Z)-1,3-bis(trimethylsilyl)alk-3-en-1-ynes 2, which underwent a desilylation reaction to afford (Z)-3-(trimethylsilyl)alk-3-en-1-ynes 3 in good yields. (IE,3Z)-1-Arylseleno-3-(trimethylsilyl)-substituted 1,3-dienes 5 could be synthesized stereoselectively via hydrozirconation of (Z)-3-(trimethylsilyl)alk-3-en-1-ynes 3, followed by trapping with arylselenenyl bromides.