Stereoselective reduction of the ketone group in α-allyl β-keto esters
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| 024 | 7 | 0 | |a 10.1134/S1070428015090067 |2 doi |
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| 245 | 0 | 0 | |a Stereoselective reduction of the ketone group in α-allyl β-keto esters |h [Elektronische Daten] |c [V. Boev, A. Moskalenko, S. Belopukhov, N. Przheval'skii] |
| 520 | 3 | |a Stereoselective reduction of the ketone carbonyl group in α-allyl-substituted β-keto esters with sodium tetrahydridoborate in the presence of 2 equiv of MnCl2 quantitatively afforded the corresponding syn-isomeric alcohols. The reduction of the same substrates with L-selectride [LiBH(s-Bu)3] in anhydrous THF was characterized by low chemoselectivity, and anti-isomeric alcohols were formed in about 50% yield. Under analogous conditions, α-allyl ketones smoothly reacted with L-selectride to give syn-isomeric alcohols in quantitative yield. The corresponding anti isomers were synthesized by the Mitsunobu reaction of the syn isomers with formic acid, followed by alkaline hydrolysis. | |
| 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 51/9(2015-09-01), 1253-1260 |x 1070-4280 |q 51:9<1253 |1 2015 |2 51 |o 11178 | |
| 856 | 4 | 0 | |u https://doi.org/10.1134/S1070428015090067 |q text/html |z Onlinezugriff via DOI |
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| 900 | 7 | |a Metadata rights reserved |b Springer special CC-BY-NC licence |2 nationallicence | |
| 908 | |D 1 |a review-article |2 jats | ||
| 949 | |B NATIONALLICENCE |F NATIONALLICENCE |b NL-springer | ||
| 950 | |B NATIONALLICENCE |P 856 |E 40 |u https://doi.org/10.1134/S1070428015090067 |q text/html |z Onlinezugriff via DOI | ||
| 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 51/9(2015-09-01), 1253-1260 |x 1070-4280 |q 51:9<1253 |1 2015 |2 51 |o 11178 | ||