Asymmetric Synthesis of Acyclic 1,3-Amino Alcohols by Reduction of N-Sulfinyl β-Amino Ketones. Formal Synthesis of (−)-Pinidinol and (+)- Epipinidinol
- 6 November 2008
- journal article
- research article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 73 (24) , 9619-9626
- https://doi.org/10.1021/jo801653c
Abstract
Stereoselective reduction of acyclic N-sulfinyl β-amino ketones with (LiEt3BH) and Li(t-BuO)3AlH, 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 β-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.Keywords
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