References
- Katsuki , T. and Sharpless , K. B. 1980 . J. Am. Chem. Soc. , 102 : 5974 – 5976 .
- Martin , V. S. , Woodard , S. C. , Katsuki , T. , Yamada , Y. , Ikeda , M. and Sharpless , K. B. 1981 . J. Am. Chem. Soc. , 103 : 6237 – 6240 .
- Pfenninger , A. 1986 . Synthesis , : 89
- Finn , M. G. and Sharpless , K. B. 1985 . Asymmetric Synthesis , Edited by: Morrison , J. D. vol. 5 , 247 New York : Academic Press . Chapter 8
- Abstracted from Ph.D. thesis entitled “Synthesis of Some Biologically Active Compounds” submitted by P. Yadagiri (1985) in the University of Pune, Poona, India. When this work was in progress K.C. Nicolau has made use of asymmetric epoxtda-tion on a similar substrate to prepare a chiron for the synthesis of tetrahydrofuran moiety. However its scope and generality has not been defined. See R.E. Dolle & K.C. Nicolau, J. Am. Chem. Soc., 107, 1691–1694(1983).
- Sharpless , K. B. , Woodard , S. C. and Finn , M. G. 1983 . Pure and Appl. Chem. , 55 : 1823
- All the compounds gave the satisfactory chemical analysis.
- Dale , J. A. , Dull , D. L. and Mosher , H. S. 1973 . J. Org. Chem. , 38 : 2143
- Mori , K. , Nakada , T. and Ebata , T. 1981 . Tetrahedron , 37 : 1343
- Normally ‘S’ enantiomer reacts faster in allylic alcohols with (+) DIPT but in the substrate under study ‘R’ enantiomer reacts faster with (+) DIPT because acetylenic moiety has higher priority over olefinic group as per sequence rules.
- Mihelich , E. D. 1979 . Tetrahedron Lett. , 49 : 4729 3 was epoxidised with mCPBA and erythro/threo ratio of the corresponding epoxy alcohol was determined by PMR. The tertiary proton in erythro series appears at 4.5 (multiplet) while in threo series at 4.2. In epoxy acetates the same proton appears at 5.52 and 5.14 for erythro and threo products respectively. For references related to PMR study of erythro/threo see. B.E. Rossiter, T.R. Verhoeven and K.B. Sharpless, Tetrahedron Lett., 49, 4733 (1979)
- Part of the work was carried out at National Chemical Laboratory, Pune, India.