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A facile stereoselective synthesis of difunctionalized 1,3-dienes containing tin and halogen via hydrozirconation of (Z)-3-(tributylstannyl)alk-3-en-1-ynes |
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| Authors: | Ming-Zhong Cai Yue Wang |
| Affiliation: | a School of Chemistry and Chemical Engineering, Jiangxi Normal University, Nanchang 330027, PR China b Department of Chemistry, Jiujiang University, Jiujiang 332000, PR China |
| Abstract: | Sonogashira coupling of (E)-α-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. |
| Keywords: | (E)-α-Iodovinylstannane Difunctionalized 1,3-diene Sonogashira coupling Hydrozirconation Stereoselective synthesis |
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