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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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Published in: | Russian journal of organic chemistry 2015-04, Vol.51 (4), p.493-497 |
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container_end_page | 497 |
container_issue | 4 |
container_start_page | 493 |
container_title | Russian journal of organic chemistry |
container_volume | 51 |
creator | Boev, V. I. Moskalenko, A. I. Belopukhov, S. L. Przheval’skii, N. M. |
description | 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. |
doi_str_mv | 10.1134/S1070428015040053 |
format | article |
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-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
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R
,4
S
)-3-allyl-4-hydroxypiperidine-1-carboxylates (
cis
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trans
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R
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-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
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trans
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R
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R
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-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.</abstract><cop>Moscow</cop><pub>Pleiades Publishing</pub><doi>10.1134/S1070428015040053</doi><tpages>5</tpages></addata></record> |
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subjects | Chemistry Chemistry and Materials Science Organic Chemistry |
title | Stereoselective syntheses of substituted tert-butyl 3-allyl-4-hydroxypiperidine-1-carboxylate |
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