A facile stereoselective synthesis of difunctionalized 1,3-dienes containing tin and halogen via hydrozirconation of (Z)-3-(tributylstannyl)alk-3-en-1-ynes

作者：Cai Ming Zhong^*; Wang Yue; Wang Ping Ping

来源：Journal of Organometallic Chemistry, 2008, 693(17): 2954-2958.

DOI：10.1016/j.jorganchem.2008.06.002

• (E)-alpha-iodovinylstannane
• difunctionalized 1,3-diene
• sonogashira coupling
• hydrozirconation
• stereoselective synthesis

Sonogashira coupling of ( E)- a- iodovinylstannanes 1 with ( trimethylsilyl) acetylene gave ( Z)- 1-( trimethylsilyl)3-( tributylstannyl) alk- 3- en- 1- ynes 2, which underwent a desilylation reaction to afford ( Z)- 3-( tributylstannyl) alk- 3- en- 1- ynes 3 in high yields. ( 1E, 3Z)- 1- Halo- 3-( tributylstannyl)- substituted 1,3- dienes 5 could be synthesized stereoselectively via hydrozirconation of ( Z)- 3-( tributylstannyl) alk- 3- en- 1- ynes 3, followed by trapping with iodine or NBS.

• 出版日期2008-8-15
• 单位江西师范大学; 九江学院