138608-02-3Relevant academic research and scientific papers
Zinc Acetate Catalyzed Enantioselective Reductive Aldol Reaction of Ketones
W?glarz, Izabela,Szewczyk, Marcin,Mlynarski, Jacek
supporting information, p. 1532 - 1536 (2020/02/05)
A highly enantioselective method for the synthesis of β-hydroxy esters via reductive aldol reaction of acrylates with aryl and heteroaromatic ketones is described. In situ generated catalyst composed of zinc acetate and chiral diamine afforded enantioenri
Efficient syntheses of four stable-isotope labeled (1R)-menthyl (1S,2S)-(+)-2-phenylcyclopropanecarboxylates
Keliher, Edmund J.,Burrell, Richard C.,Chobanian, Harry R.,Conkrite, Karina L.,Shukla, Rajesh,Baldwin, John E.
, p. 2777 - 2784 (2008/09/16)
Many carbenoid cyclopropanation reactions promoted by chiral catalysts give product mixtures reflecting impressive diastereo- and enantioselectivities. Few provide a single chiral product efficiently. This limitation has been overcome in cyclopropanations of styrene and isotopically labeled styrenes with α-diazoacetates. Convenient syntheses on a 20 g scale of each of four chiral isotopically labeled (1R)-menthyl (1S,2S)-2- phenylcyclopropanecarboxylates (the 1-d-3-13C, 1,(3S)-d2, 1,2,(3S)-d3, and 1,3,3-d3 isotopomers) of better than 99% ee have been realized. The Royal Society of Chemistry 2006.
Organic chemistry: Preparative synthesis of the Corey chiral controller for enantioselective dihydroxylation of olefins
Lapitskaya,Pivnitsky
, p. 96 - 100 (2007/10/03)
A five-step synthesis of both enantiomers of 1,2-di(2,4,6-trimethylbenzylamino)-1,2-diphenylethane, i.e., Corey (R,R)- and (S,S)-controllers for enantioselective dihydroxylation of olefins by osmium tetroxide, starting from α,α'-diphenylglyoxime, has been developed. The key operations in the synthesis are the optical resolution of intermediate rac-1,2-diamino-1,2-diphenylethane into two enantiomers using only (R,R)-tartaric acid and the subsequent enhancement of the enantiomeric purity to >98% by crystallizations of the corresponding Schiff's bis-bases. Analysis of the enantiomeric purity of the controllers can be easily performed using 1H NMR spectra of their salts with (R)-α-methoxy-α-(trifluoromethyl)phenylacetic acid (Mosher R-acid).
