beta-Hydroxy Ketone Reduction

  • The mixture from the aldol reaction was separated by prep HPLC and the major

    diasteromer was reduced. The product ratio from the reduction was calculated from HPLC.

    This selectivity in the reduction step has been used in the synthesis of other indolizidines.2

    Amino Alcohol Isolation

    The relative stereochemistry of the amino alcohol (14) is currently under investigation.


    We thank the EPSRC for financial support.


    1. M.E. Garst, J.N. Bonfiglio, D.H. Grudoski and J. Marks, J. Org. Chem., 1980, 45, 2307. 2. T. Gallagher, M. Giles, R.S. Subramanian and M.S. Hadley, J. Chem. Soc., Chem. Commun., 1992,166. S.H.J. Thompson, R.S. Subramanian, J.K. Roberts, M.S. Hadley and T. Gallagher, J. Chem. Soc., Chem. Commun.,1994,933. 3. T. Mukaiyama, K. Banno and K. Narasaka, J. Am. Chem. Soc., 1979, 96, 7503. 4. E. Nakamura, M. Shimizu, I. Kuwajima, J. Sakata, K. Yokoyama and R. Noyori, J. Am. Chem. Soc., 1983, 48, 932. 5. S. Murata, M. Suzuki and R. Noyori, Tetrahedron, 1988, 44, 4259. 6. F. G. Bordwell, T. Gallagher, X. Zhang, J. Am. Chem. Soc., 1991, 113, 3405.