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Direct asymmetric synthesis of oxazolines from olefins using a chiral nitridomanganese complex: a novel three-component coupling leading to chiral oxazolines

2001; Elsevier BV; Volume: 42; Issue: 51 Linguagem: Inglês

10.1016/s0040-4039(01)01963-3

1873-3581

Satoshi Minakata, Masaaki Nishimura, Tôru Takahashi, Yoji Oderaotoshi, Mitsuo Komatsu,

Catalytic C–H Functionalization Methods

A new synthetic method for chiral oxazolines has been developed by N1 unit transfer to olefins using a chiral nitridomanganese complex. When trans-disubstituted styrenes were treated with chiral complex 1 in the presence of an acid chloride, oxazolines were obtained with high enantioselectivities (up to 92% ee). Furthermore, the produced oxazolines could be easily converted into β-amino alcohols, which are ephedrine derivatives.