Synthesis of 1',2',3',4',5'-pentamethyl-3,4-diphenylazaferrocene and its enantioselective C-2 functionalization via (-)-sparteine-mediated lithiation.

[摘要]：Lithiation of 1',2',3',4',5'-pentamethyl-3,4-diphenylazaferrocene (9) with sec-BuLi/(-)-sparteine (2) in Et2O at -78?followed by quenching with electrophiles gave the C-2 functionalized azaferrocenes in good enantioselectivities (up to 79% ee). In contrast, treatment of 9 with tert-BuLi/(-)-sparteine (2) leaded to lateral lithiation at the Me group of cyclopentadienyl ring. The crystal structure of hydroxymethyldiphenyl azaferrocene was detd.

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