Abstract
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 intermediaterac-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 using1H NMR spectra of their salts with (R)-α-methoxy-α-(trifluoromethyl)phenylacetic acid (MosherR-acid).
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Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 1, pp. 101–105, January, 1997.
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Lapitskaya, M.A., Pivnitsky, K.K. Preparative synthesis of the Corey chiral controller for enantioselective dihydroxylation of olefins. Russ Chem Bull 46, 96–100 (1997). https://doi.org/10.1007/BF02495355
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DOI: https://doi.org/10.1007/BF02495355