铟介导的醛、酮和亚磺酰亚胺与2-(烷氧基)烯丙基溴的烯丙基化反应。
Indium-mediated allylation of aldehydes, ketones and sulfonimines with 2-(alkoxy)allyl bromides.
作者信息
Dhanjee Heemal, Minehan Thomas G
机构信息
Department of Chemistry and Biochemistry, California State University, Northridge 18111 Nordhoff, Street, Northridge, CA 91330.
出版信息
Tetrahedron Lett. 2010 Oct 20;51(42):5609-5612. doi: 10.1016/j.tetlet.2010.08.064.
Abstract
2-(Alkoxy)propenyl bromides are readily prepared from 1,3-dibromo-2-propanol in a two-step sequence involving hydroxyl protection and sodium hydride-induced dehydrobromination. Indium-mediated allylation of aldehydes, ketones, and sulfonimines with 2-(alkoxy)propenyl bromides furnishes the corresponding homoallylic alcohols and sulfonamines in good yields. The products can be easily transformed into β-hydroxy ketones and esters, as well as substituted dihydropyrans and protected β-amino acids. Chiral 2-(alkoxy)propenyl halides, derived from (-)-menthol and D-glucal, furnish diastereomerically enriched products.
摘要
2-(烷氧基)丙烯基溴可通过两步反应由1,3-二溴-2-丙醇轻松制备，这两步反应包括羟基保护和氢化钠引发的脱溴反应。铟介导的醛、酮和磺亚胺与2-(烷氧基)丙烯基溴的烯丙基化反应能以良好的产率提供相应的高烯丙醇和磺酰胺。产物可轻松转化为β-羟基酮和酯，以及取代的二氢吡喃和保护的β-氨基酸。由(-)-薄荷醇和D-葡糖醛衍生的手性2-(烷氧基)丙烯基卤化物可提供非对映体富集的产物。
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