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E. Corey, R. Imwinkelried, S. Pikul, Y. Xiang (1989)
Practical enantioselective Diels-Alder and aldol reactions using a new chiral controller systemJournal of the American Chemical Society, 111
F. Feist
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E. Corey, P. Jardine, S. Virgil, P. Yuen, R. Connell (1989)
Enantioselective vicinal hydroxylation of terminal and E-1,2-disubstituted olefins by a chiral complex of osmium tetraoxide. An effective controller system and a rational mechanistic modelJournal of the American Chemical Society, 111
K. Sharpless, W. Amberg, Y. Bennani, G. Crispino, J. Hartung, Kyu‐Sung Jeong, H. Kwong, Kouhei Morikawa, Z. Wang (1992)
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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).
Russian Chemical Bulletin – Springer Journals
Published: Aug 30, 2006
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