Stereoselective syntheses of substituted tert-butyl 3-allyl-4-hydroxypiperidine-1-carboxylate

tert -Butyl 3-allyl-4-oxopiperidine-1-carboxylate and its derivatives substituted at the 3-position and in the allylic fragment reacted with L-selectride in anhydrous tetrahydrofuran to give tert -butyl (3 R ,4 S )-3-allyl-4-hydroxypiperidine-1-carboxylates ( cis isomers) in quantitative yield. The...

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Bibliographic Details
Published in:Russian journal of organic chemistry 2015-04, Vol.51 (4), p.493-497
Main Authors: Boev, V. I., Moskalenko, A. I., Belopukhov, S. L., Przheval’skii, N. M.
Format: Article
Language:English
Subjects:
Chemistry
Chemistry and Materials Science
Organic Chemistry
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Summary:tert -Butyl 3-allyl-4-oxopiperidine-1-carboxylate and its derivatives substituted at the 3-position and in the allylic fragment reacted with L-selectride in anhydrous tetrahydrofuran to give tert -butyl (3 R ,4 S )-3-allyl-4-hydroxypiperidine-1-carboxylates ( cis isomers) in quantitative yield. The Mitsunobu reaction of the latter with formic or benzoic acid, followed by alkaline hydrolysis, afforded the corresponding trans (3 R ,4 R ) isomers.
ISSN:1070-4280
1608-3393
DOI:10.1134/S1070428015040053