Asymmetric Synthesis of Acyclic 1,3-Amino Alcohols by Reduction of N-Sulfinyl β-Amino Ketones. Formal Synthesis of (-)-Pinidinol and (+)-Epipinidinol

被引：65

作者：

Davis, Franklin A. ^{[1
]}

Gaspari, Paul M. ^{[1
]}

Nolt, Brad M. ^{[1
]}

Xu, Peng ^{[1
]}

机构：

[1] Temple Univ, Dept Chem, Philadelphia, PA 19096 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2008年 / 73卷 / 24期

关键词：

D O I：

10.1021/jo801653c

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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.

引用

页码：9619 / 9626

页数：8

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