ABSTRACT

The enantioselective deprotonation reaction has been applied to the synthesis of a number of key intermediates, which can be elaborated to important biologically active compounds such as prostaglandin (10). In most cases, the procedure requires more than a stoichiometric amount of chiral bases. Thus, the development of an effective catalytic system using a chiral lithium amide is currently a significant challenge in synthetic organic chemistry. There have been only a few reports where a chirallithium amide has been employed in catalytic amount (1114), and only three reports where the application has been used for the rearrangement of an epoxide to allylic alcohol (11-13). The first such study by Asami et al. (11), using catalytic amount of a series of chirallithium amides derived from (S)- proline reported a maximum of 79% ee for the conversion. In a subsequent study, however, they improved the ee to 94% (13}. While another study with his-lithium amide base from chiral diamines reported the ee of up to 77% (12).