Synthesis of tryptophans by alkylation of chiral glycine enolate equivalents with quaternary gramines

Reinfelds, Matiss; Kalinins, Konstantins; Katkevica, Dace; Zemribo, Ronalds; Katkevics, Martins

Synthesis of tryptophans by alkylation of chiral glycine enolate equivalents with quaternary gramines

2015

Reinfelds, Matiss | Kalinins, Konstantins | Katkevica, Dace | Zemribo, Ronalds | Katkevics, Martins

Quaternary gramines were found to be a suitable source of the 3-methylindole fragment for diastereoselective alkylation. The best yields and stereoselectivity were obtained for the alkylation of a chiral William’s morpholinone enolate. Based on this transformation, a general method for the synthesis of enantiopure, indole ring substituted tryptophan derivatives was developed with good overall yields.

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