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The external chiral ligand mediated asymmetric reaction of thiazolyllithium with aldimines was examined. The amino ether (5) gave rise to relatively high selectivity in the reaction of phenylimine, and sparteine (6) provided high selectivity in the reaction of imines bearing an α-methylene group. The reaction was applied to the synthesis of (S)-Doe, a component of antileukemic marine natural product,...
The chiral ligand mediated enantioselective reaction of methyllithium with furylimines was investigated in the presumed 1,4- and 1,2-addition manners. The imines bearing a phosphinoyl or sulfonyl group on the imine nitrogen atom gave rather poor enantioselectivity. On the other hand, the imines bearing a 2-substituted anisidine moiety were found to be the appropriate substrate, giving the corresponding...
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