Highly efficient synthesis of stereodefined multisubstituted 1,4-dicyano- and 1-cyano-1,3-butadienes and their reactions with organolithium reagents |
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Authors: | Wang Congyang Wang Chao Wang Qifeng Wang Zhihui Sun Hui Guo Xiangyu Xi Zhenfeng |
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Affiliation: | Beijing National Laboratory for Molecular Sciences (BNLMS), Ministry of Education, College of Chemistry, Peking University, Beijing 100871, China. |
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Abstract: | Stereodefined multisubstituted 1-cyano- and 1,4-dicyano-1,3-butadiene derivatives were obtained in excellent yields of the isolated product from their corresponding monohalo- and dihalobutadienes and CuCN. This reaction proceeded with high stereoselectivity and retention of the stereochemistry of the starting halobutadienes. A study of the utility of the thus-obtained 1-cyano- and 1,4-dicyano-1,3-butadiene derivatives was demonstrated by their reactions with organolithium reagents. 2H-Pyrrole or iminocyclopentadiene derivatives were formed in high yields from 1-cyano-4-halo-1,3-butadienes and organolithium reagents. When 1,4-dicyano-1,3-butadienes were treated with organolithium reagents followed by trapping with electrophiles, a tandem process took place to afford 2H-pyrrolyl nitriles in excellent yields. Reduction of 1,4-dicyano-1,3-butadiene derivatives with LiAlH4 showed novel reaction patterns relative to normal nitriles. |
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Keywords: | butadienes lithiation nitriles stereoselectivity synthetic methods |
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