Tetrahedron Letters p. 2545 - 2548 (1984)
Update date:2022-08-05
Topics:
Seebach, Dieter
Aebi, Johannes D.
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.
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