α-ALKYLATION OF SERINE WITH SELF-PRODUKTION OF THE CENTER OF CHIRALITY

Article abstract of DOI:10.1016/S0040-4039(01)81227-2

The lithium enolate 6 of methyl (2R,4S)-2-t-butyl-3-formyl-oxazolidine-4-carboxylate (4b) derived from (S)-(+)-serine can be generated with LDA in THF solution at -75 deg C.Alkylations (9) and hydroxyalkylations (10,11) occur preferentially (>95:5) from the Re-face of the donor center (relative topicity lk).This stereochemical course is derived from the absolute configuration of 2-deuterio- and 2-methyl-serine (12,13) obtained through the enolate 6.