caa a22 4500 605529000 CHVBK 20210128100816.0 cr unu---uuuuu 210128e20150901xx s 000 0 eng 10.1134/S1070428015090067 doi (NATIONALLICENCE)springer-10.1134/S1070428015090067 Stereoselective reduction of the ketone group in α-allyl β-keto esters [Elektronische Daten] [V. Boev, A. Moskalenko, S. Belopukhov, N. Przheval'skii] 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. Pleiades Publishing, Ltd., 2015 Boev V. Timiryazev Moscow Agricultural Academy Russian State Agrarian University, Timiryazevskaya ul. 49, 127550, Moscow, Russia aut Moskalenko A. Timiryazev Moscow Agricultural Academy Russian State Agrarian University, Timiryazevskaya ul. 49, 127550, Moscow, Russia aut Belopukhov S. Timiryazev Moscow Agricultural Academy Russian State Agrarian University, Timiryazevskaya ul. 49, 127550, Moscow, Russia aut Przheval'skii N. Timiryazev Moscow Agricultural Academy Russian State Agrarian University, Timiryazevskaya ul. 49, 127550, Moscow, Russia aut Russian Journal of Organic Chemistry Pleiades Publishing 51/9(2015-09-01), 1253-1260 1070-4280 51:9<1253 2015 51 11178 https://doi.org/10.1134/S1070428015090067 text/html Onlinezugriff via DOI BK010053 XK010053 XK010000 Metadata rights reserved Springer special CC-BY-NC licence nationallicence 1 review-article jats NATIONALLICENCE NATIONALLICENCE NL-springer NATIONALLICENCE 856 40 https://doi.org/10.1134/S1070428015090067 text/html Onlinezugriff via DOI NATIONALLICENCE 700 1- Boev V. Timiryazev Moscow Agricultural Academy Russian State Agrarian University, Timiryazevskaya ul. 49, 127550, Moscow, Russia aut NATIONALLICENCE 700 1- Moskalenko A. Timiryazev Moscow Agricultural Academy Russian State Agrarian University, Timiryazevskaya ul. 49, 127550, Moscow, Russia aut NATIONALLICENCE 700 1- Belopukhov S. Timiryazev Moscow Agricultural Academy Russian State Agrarian University, Timiryazevskaya ul. 49, 127550, Moscow, Russia aut NATIONALLICENCE 700 1- Przheval'skii N. Timiryazev Moscow Agricultural Academy Russian State Agrarian University, Timiryazevskaya ul. 49, 127550, Moscow, Russia aut NATIONALLICENCE 773 0- Russian Journal of Organic Chemistry Pleiades Publishing 51/9(2015-09-01), 1253-1260 1070-4280 51:9<1253 2015 51 11178