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An efficient Bi/NH4I-mediated addition reaction for the highly diastereoselective synthesis of homoallylic alcohols in aqueous media |
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| Authors: | Zhen Wu Xue-Xin Feng Qing-Dong Wang Xuan-Yu Liu Weidong Rao Jin-Ming Yang Zhi-Liang Shen |
| Institution: | School of Chemistry and Molecular Engineering, Nanjing Tech University, Nanjing 211816, China; School of Pharmacy, Yancheng Teachers University, Yancheng 224007, China; Jiangsu Key Laboratory of Biomass-based Green Fuels and Chemicals, College of Chemical Engineering, Nanjing Forestry University, Nanjing 210037, China |
| Abstract: | An efficient water-based bismuth-mediated addition reaction of carbonyl compound with cyclic allylic halide was developed. The reactions proceeded smoothly in aqueous DMF in the presence of ammonium iodide to afford the corresponding syn-homoallylic alcohols in moderate to good yields with excellent diastereoselectivities (>99:1 syn:anti). Reversal of product diastereoselectivity was observed when heteroaryl aldehyde possessing an adjacent chelating nitrogen atom was employed as substrate. |
| Keywords: | Bismuth Ammonium iodide Water Homoallylic alcohol Diastereoselectivity |
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