Catalytic asymmetric oxidation of tert-butyl disulfide. Synthesis of tert-butanesulfinamides, tert-butyl sulfoxides, and tert-butanesulfinimines
DA Cogan, G Liu, K Kim, BJ Backes…
文献索引：Cogan, Derek A.; Liu, Guangcheng; Kim, Kyungjin; Backes, Bradley J.; Ellman, Jonathan A. Journal of the American Chemical Society, 1998 , vol. 120, # 32 p. 8011 - 8019
The first example of the catalytic asymmetric oxidation of tert-butyl disulfide (1) is described. The product, tert-butyl tert-butanethiosulfinate (2) is obtained with 91% enantiomeric excess in yields of≥ 92% on scales as large as 1 mol. The application of H2O2 as stoichiometric oxidant in the presence of 0.25 mol% of VO (acac) 2 and 0.26 mol% of a chiral Schiff base ligand, 6a, is both convenient and cost-effective. Thiosulfinate ester 2 is chemically and ...
