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Cu-Catalyzed Divergent Transformations of Allenylethylene Carbonates with Diboron Reagents
Sijie Chen1, Xiaojie Su1, Yujie Dong1
1Department of Chemistry and Innovation Center of Pesticide Research, China Agricultural University, 2 Yuanmingyuan West Road, Beijing 100193, P. R. China.
Abstract:
Divergent transformations of allenylethylene carbonates with diboron reagents catalyzed by copper are disclosed. By using CuCl/IPr·HCl as the catalyst, the allenylethylene carbonates react with B2hex2 to afford 2,4-dien-1-ols as the product in the presence of Cs2CO3 as the base, PrOH as the additive, and 1,4-dioxane as the solvent. And they react with B2pin2 to form boronic half acids in the presence of NaOBu as the base, water as the additive, and THF as the solvent. The reactions afford corresponding products in good stereoselectivities and yields, and further derivatizations of boronic half acids and study of the mechanism are also demonstrated.
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