Reversible stereocontrol in the Lewis acid promoted reaction of alkoxyaldehydes toward various allyltins |
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Authors: | Yutaka Nishigaichi Akio Takuwa |
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Affiliation: | Department of Material Science, Faculty of Science and Engineering, Shimane University, 1060 Nishikawatsu-cho, Matsue, Shimane 690-8504, Japan |
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Abstract: | In the reactions of variously substituted allyltin reagents toward achiral alkoxyaldehydes, one of the diastereomeric homoallyl alcohols was stereoselectively obtained by the help of BF3, while TiCl4 preferentially gave the other diastereomer, though (E)- and (Z)-3-monoalkylallyltin reagents were exceptional. This reversible diastereoselectivity can be explained by the coordination geometry (anti or syn) of the Lewis acids toward alkoxyaldehydes. |
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Keywords: | allylation chelation diastereoselection stereocontrol tin and compounds |
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