461045-28-3Relevant academic research and scientific papers
Organocatalytic Mukaiyama Mannich Reactions of 2,5-Bis(trimethylsilyloxy)furan
Laws, Stephen W.,Howard, Sara Y.,Mato, Raquel,Meng, Shuyu,Fettinger, James C.,Shaw, Jared T.
supporting information, p. 5073 - 5077 (2019/07/03)
The organocatalytic synthesis of densely substituted mono- and bis-?-lactams involving the Mukaiyama Mannich addition of 2,5-bis(trimethylsilyloxy)furan to imines is described. Use of a ditoluenesulfonylimide catalyst produces ?-lactams from monoaddition, whereas a more acidic catalyst (triflic acid) produces fused bis-lactams from double addition. Optimized organocatalytic conditions allow for the selective synthesis of either desired core as well as the one-pot, multicomponent assembly of the trisubstituted monolactams from aldehydes, amines, and bis-trimethylsilyloxyfuran. An examination of chiral acids found these organocatalysts to be highly active and diastereoselective in the monoaddition reaction, albeit with no enantioselectivity.
Toward lead-oriented synthesis: One-pot version of castagnoli condensation with nonactivated alicyclic anhydrides
Ryabukhin, Sergey V.,Panov, Dmitriy M.,Granat, Dmitry S.,Ostapchuk, Eugeniy N.,Kryvoruchko, Dmitriy V.,Grygorenko, Oleksandr O.
, p. 146 - 153 (2014/04/03)
One-pot variation of Castagnoli condensation, that is, reaction of cyclic anhydrides, amines, and aldehydes, has been developed as a combinatorial approach to 1,2-disubstituted 5-oxopyrrolidine- and 6-oxopiperidine-3-carboxylic acids, as well as their benzo-analogues. Utility of the method to multigram preparation of building blocks and synthetic intermediates was also demonstrated. The final products are obtained in high yields and diastereoselectivity. The method fits well in the concept of lead-oriented synthesis; in particular, it can be used for the design of lead-like compound libraries, even if the strictest cut-offs are applied to the physicochemical properties of their members.
Enantiomers of (2R*,3R*)-1-methyl-5-oxo-2-phenyltetrahydro-1H-pyrrolidine-3-carboxylic acid as novel chiral resolving agents
Piwowarczyk, Katarzyna,Zawadzka, Anna,Roszkowski, Piotr,Szawkalo, Joanna,Leniewski, Andrzej,Maurin, Jan K.,Kranz, Darius,Czarnocki, Zbigniew
, p. 309 - 317 (2008/09/19)
A series of (2R*,3R*)-1-methyl-5-oxo-2-aryltetrahydro-1H-pyrrolidine-3-carboxylic acids were prepared and their structures were proven with X-ray crystallography. Racemic acid 5 has been resolved into enantiomers (2S,3S)-5 and (2R,3R)-5 by the formation of diastereomeric salts with brucine 9 and strychnidine 10, respectively. The ability of these enantiomers to serve as chiral discriminating agents was demonstrated by the chromatographic separation of diastereomeric amides and esters. Also, some preliminary results on the enantioselective reduction of prochiral imines with sodium borohydride modified by (2R,3R)-5 were collected.
HIGHLY ACCELERATED REACTIONS IN A MICROWAVE OVEN : SYNTHESIS OF HETEROCYCLES
Bose, Ajay K.,Manhas, Maghar S.,Ghosh, Malay,Raju, Vegesna S.,Tabei, Keiko,Urbanczyk-Lipkowska, Zofia
, p. 741 - 744 (2007/10/02)
Efficient synthesis of a wide variety of heterocycles on 0.1 to 200 g scale was conducted in organic solvents in a commercial microwave oven in a few minutes at a low energy level.Erlenmeyer flasks were adequate reaction vessels since neither high pressure nor high temperature were involved.Fast monitoring of synthetic reactions was achieved by tlc separation and transfer of tlc spot material directly to a solids probe of a chemical ionization mass spectrometer.Microwave Oven-induced Reaction Enhancement (MORE) chemistry is not due to thermolysis: one reaction was conducted successfully in a reaction vial encased in a block of ice.
