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

Verfasser / Beitragende:
[V. Boev, A. Moskalenko, S. Belopukhov, N. Przheval'skii]
Ort, Verlag, Jahr:
2015
Enthalten in:
Russian Journal of Organic Chemistry, 51/4(2015-04-01), 493-497
Format:
Artikel (online)
ID: 605530246
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024 7 0 |a 10.1134/S1070428015040053  |2 doi 
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245 0 0 |a Stereoselective syntheses of substituted tert -butyl 3-allyl-4-hydroxypiperidine-1-carboxylate  |h [Elektronische Daten]  |c [V. Boev, A. Moskalenko, S. Belopukhov, N. Przheval'skii] 
520 3 |a 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 (3R,4S)-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 (3R,4R) isomers. 
540 |a Pleiades Publishing, Ltd., 2015 
700 1 |a Boev  |D V.  |u "Timiryazev Moscow Agricultural Academy” Russian State Agrarian University, Timiryazevskaya ul. 49, 127550, Moscow, Russia  |4 aut 
700 1 |a Moskalenko  |D A.  |u "Timiryazev Moscow Agricultural Academy” Russian State Agrarian University, Timiryazevskaya ul. 49, 127550, Moscow, Russia  |4 aut 
700 1 |a Belopukhov  |D S.  |u "Timiryazev Moscow Agricultural Academy” Russian State Agrarian University, Timiryazevskaya ul. 49, 127550, Moscow, Russia  |4 aut 
700 1 |a Przheval'skii  |D N.  |u "Timiryazev Moscow Agricultural Academy” Russian State Agrarian University, Timiryazevskaya ul. 49, 127550, Moscow, Russia  |4 aut 
773 0 |t Russian Journal of Organic Chemistry  |d Pleiades Publishing  |g 51/4(2015-04-01), 493-497  |x 1070-4280  |q 51:4<493  |1 2015  |2 51  |o 11178 
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950 |B NATIONALLICENCE  |P 700  |E 1-  |a Boev  |D V.  |u "Timiryazev Moscow Agricultural Academy” Russian State Agrarian University, Timiryazevskaya ul. 49, 127550, Moscow, Russia  |4 aut 
950 |B NATIONALLICENCE  |P 700  |E 1-  |a Moskalenko  |D A.  |u "Timiryazev Moscow Agricultural Academy” Russian State Agrarian University, Timiryazevskaya ul. 49, 127550, Moscow, Russia  |4 aut 
950 |B NATIONALLICENCE  |P 700  |E 1-  |a Belopukhov  |D S.  |u "Timiryazev Moscow Agricultural Academy” Russian State Agrarian University, Timiryazevskaya ul. 49, 127550, Moscow, Russia  |4 aut 
950 |B NATIONALLICENCE  |P 700  |E 1-  |a Przheval'skii  |D N.  |u "Timiryazev Moscow Agricultural Academy” Russian State Agrarian University, Timiryazevskaya ul. 49, 127550, Moscow, Russia  |4 aut 
950 |B NATIONALLICENCE  |P 773  |E 0-  |t Russian Journal of Organic Chemistry  |d Pleiades Publishing  |g 51/4(2015-04-01), 493-497  |x 1070-4280  |q 51:4<493  |1 2015  |2 51  |o 11178