108692-67-7Relevant academic research and scientific papers
Thiocrown ether additive effects on diastereoselectivity of the lipase- catalyzed reaction: Preparation of optically active 3-hydroxy-2- methylalkanenitriles through a double enzymatic reaction strategy
Mitsukura, Koichi,Choraku, Hiroko,Da, San Thi,Itoh, Toshiyuki
, p. 1589 - 1595 (1999)
The additive effect on diastereoselectivity towards the lipase-catalyzed hydrolysis of acetates of 3-hydroxy-2-methyl-or 3-hydroxy-2- ethylalkanenitriles has been investigated. Diastereoselectivity was not influenced by thiocrown ether additives, although a significant modification of enantioselectivity was observed. Origin of the diastereoselectivity of the lipase-catalyzed reaction was thus evidently different from that of enantioselectivity. Based on these results, an easy preparation of optically active 3-hydroxy-2-methylpentanenitrile and 3-hydroxy-2-methylbutanenitrile have been demonstrated through lipase-catalyzed reaction by a double enzymatic reaction strategy.
SYNTHESIS OF ALL FOUR POSSIBLE ENANTIOMERS OF SITOPHILATE AGGREGATION PHEROMONE OF THE GRANARY WEEVIL
Cheskis, B. A.,Shpiro, N. A.,Moiseenkov, A. M.
, p. 2205 - 2211 (2007/10/02)
An efficient synthesis of the 3-pentyl ester of 2S-methyl-3R-hydroxypentanoic acid (sitophilate) and its 2S,3S-, 2R,3R-, and 2R,3S-isomers has been carried out starting from the available 2R-methyl-3-butenyl acetate as sole monochiral precursor.
DIASTEREO- AND ENANTIOSELECTIVE PREPARATION OF β-ALKYLHOMOALLYLIC ALCOHOLS SYNTHESIS OF SERRICORNIN AND CORYNOMYCOLIC ACID
Kobayashi, Yuichi,Kitano, Yasunori,Takeda, Yoshiyuki,Sato, Fumie
, p. 2937 - 2944 (2007/10/02)
A new and efficient method for the preparation of four possible stereoisomers of β-alkylhomoallylic alcohols 1 has been developed which is based on the diastereoselective addition of nucleophiles to optically active α-alkyl-β-trimethylsilyl-β,γ-unsaturate
DIASTEREOSELECTION IN 1,3-O- TO -C-ALKYL MIGRATION REACTION OF 1-ALKENYL ALKYL ACETALS CATALYZED BY BORON TRIFLUORIDE ETHERATE
Takahashi, Mitsuru,Suzuki, Hiroharu,Moro-Oka, Yoshihiko,Ikawa, Tsuneo
, p. 4031 - 4034 (2007/10/02)
Remarkable diastereoselection, with (E)-alkenyl alkyl acetal giving selectively the erythro α-alkyl-β-alkoxyaldehyde, and (Z)-acetal leading preferentially to the threo isomer, is observed in the 1,3-O- to -C-alkyl migration reaction of 1-alkenyl alkyl ac
