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

作者：Ye Xinglin; Wang Pingping; Liu Jiaqin; Cai Mingzhong^*

来源：Synthetic Communications, 2009, 39(13): 2378-2391.

DOI：10.1080/00397910802654864

• Difunctionalized 1
• 3-diene
• hydrozirconation
• (E)--iodovinylsilane
• Sonogashira coupling
• stereoselective synthesis

Sonogashira coupling of (E)--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. (1E,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.

• 出版日期2009
• 单位江西师范大学