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首页> 外文期刊>Chemistry: A European journal >Highly enantioselective approach to geminal bisphosphonates by organocatalyzed Michael-type addition of beta-ketoesters
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Highly enantioselective approach to geminal bisphosphonates by organocatalyzed Michael-type addition of beta-ketoesters

机译：β-酮酸酯的有机催化迈克尔型加成对双膦酸酯的高度对映选择性

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摘要

A valuable organocatalyzed protocol has been developed for the asymmetric synthesis of bisphosphonate derivatives, a class of pharmaceutically important molecules. Cheap and commercially available dihydroquinine effectively catalyzed conjugate additions of cyclic beta-ketoesters to ethylide-nebisphosphonate esters, leading to optically active geminal bisphosphonates, bearing an all-carbon substituted quaternary stereocenter, in high yields and enantioselectivities of up to 99% ee. Further elaborations of Michael adducts to the corresponding bisphosphonic acids or vinyl phosphonates have also been successfully performed, with conservation of optical purity.
机译：已经开发了一种有价值的有机催化方案，用于一类重要药物分子双膦酸酯衍生物的不对称合成。廉价且可商购的二氢奎宁可有效催化环状β-酮酸酯与乙叉基-双膦酸酯的共轭加成反应，从而形成具有全碳取代的季立体中心的旋光性双膦酸酯，具有高收率和高达99％ee的对映选择性。还成功地完成了迈克尔加合物对相应的双膦酸或乙烯基膦酸酯的进一步精制，同时保持了光学纯度。

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