Graduate School of Engineering, Nagoya University, Furo-cho, Chikusa, Nagoya, 464-8603, Japan.
Science. 2010 Jun 11;328(5984):1376-9. doi: 10.1126/science.1188217.
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.
在药物产品的合成中，为氧化反应而使用稀有或有毒金属是不可取的。高价碘化合物是环境友好的替代品，但它们的催化应用，特别是在不对称转化方面，受到了相当大的限制。我们在此报告了一种通过原位生成的手性季铵（次）碘盐，以过氧化氢为环境友好的氧化剂，催化酮酚的对映选择性氧化环醚化反应，生成 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具有生物活性的化合物的关键结构。
