Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 73, Issue 24, Pages 9619-9626Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo801653c
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- National Institutes of General Medical Sciences [GM 57870]
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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.
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