Quaternary Ammonium (Hypo)iodite Catalysis for Enantioselective Oxidative Cycloetherification
Quaternary Ammonium (Hypo)iodite Catalysis for Enantioselective Oxidative Cycloetherification
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DOI：
10.1126/science.1188217
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发表时间：
2010-06-11
期刊：
影响因子：
56.9
通讯作者：
Ishihara, Kazuaki
中科院分区：
文献类型：
--
作者：
Uyanik, Muhammet;Okamoto, Hiroaki;Ishihara, Kazuaki
在医药产品的合成中，希望尽量减少使用稀有或有毒金属进行氧化反应。高价碘化合物是环境友好的替代品，但它们的催化用途，特别是在不对称转化中的应用，一直相当有限。本文报道了以过氧化氢为环境友好的氧化剂，在原位生成的手性季铵盐(次)碘酸盐催化下酮苯酚的不对称氧化环醚化合成2-酰基-2，3-二氢苯并呋喃衍生物。光学活性的2-酰基2，3-二氢苯并呋喃骨架是几种生物活性化合物的关键结构。
It is desirable to minimize the use of rare or toxic metals for oxidative reactions in the synthesis of pharmaceutical products. Hypervalent iodine compounds are environmentally benign alternatives, but their catalytic use, particularly for asymmetric transformations, has been quite limited. We report here an enantioselective oxidative cycloetherification of ketophenols to 2-acyl-2,3-dihydrobenzofuran derivatives, catalyzed by in situ-generated chiral quaternary ammonium (hypo)iodite salts, with hydrogen peroxide as an environmentally benign oxidant. The optically active 2-acyl 2,3-dihydrobenzofuran skeleton is a key structure in several biologically active compounds.