Asymmetric Synthesis of Acyclic 1,3-Amino Alcohols by Reduction of N-Sulfinyl β-Amino Ketones. Formal Synthesis of (-)-Pinidinol and (+)-Epipinidinol
Asymmetric Synthesis of Acyclic 1,3-Amino Alcohols by Reduction of N-Sulfinyl β-Amino Ketones. Formal Synthesis of (-)-Pinidinol and (+)-Epipinidinol
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DOI：
10.1021/jo801653c
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发表时间：
2008-12-19
影响因子：
3.6
通讯作者：
Xu, Peng
中科院分区：
文献类型：
--
作者：
Davis, Franklin A.;Gaspari, Paul M.;Xu, Peng
分别用(LiEt3BH)和Li(t-BuO)(3)AlH立体选择性还原无环N-亚磺酰基β-氨基酮，得到具有优异选择性的反-和顺-1,3-氨基醇。开发了一种由常见的 N-亚磺酰基 β-氨基酮缩酮前体正式不对称合成羟基哌啶生物碱 (-)-pinidinol 和 (+)-epipinidinol 的方法。哌啶醇哌啶环是通过 N-亚磺酰氨基甲硅烷基保护的醇缩酮的新型酸催化级联反应形成的。
Stereoselective reduction of acyclic N-sulfinyl beta-amino ketones with (LiEt3BH) and Li(t-BuO)(3)AlH, respectively, gave anti- and syn-1,3-amino alcohols with excellent selectivity. A formal asymmetric synthesis of the hydroxy piperidine alkaloids (-)-pinidinol and (+)-epipinidinol from a common N-sulfinyl beta-amino ketone ketal precursor was developed. The pinidinol piperidine ring was formed via a novel acid-catalyzed cascade reaction of a N-sulfinylamino silyl protected alcohol ketal.