Synthetic utility of bowl-shaped tris(2,6-diphenyl-benzyl)silyl glyoxylate as a stable glyoxylate: application to highly diastereoselective aldol reactions |
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| Authors: | Seiji ShirakawaKeiji Maruoka |
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| Institution: | Department of Chemistry, Graduate School of Science, Kyoto University, Kyoto 606-8502, Japan |
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| Abstract: | A stable glyoxylate can be successfully applied to both syn- and anti-selective aldol reactions by using two different kinds of ordinary Lewis acids. Thus, treatment of bowl-shaped tris(2,6-diphenylbenzyl)silyl glyoxylate 1 with enol silyl ether under the influence of BF3·OEt2 gave syn-aldol product, while the use of TiCl4 afforded anti-aldol product with >97% selectivity. |
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| Keywords: | diastereoselectivity aldol reaction glyoxylate enol silyl ether |
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