Tetrahedron Letters p. 6251 - 6252 (1995)
Update date:2022-08-05
Topics:
Kubo, Akira
Takahashi, Masami
Kubota, Hitoshi
Nunami, Ken-Ichi
Dynamic kinetic resolution by highly stereoselective carbon-carbon bond formation utilizing 2-oxoimidazolidine-4-carboxylate as a chiral auxiliary was exploited. The reaction of tert-butyl (4S)-1-methyl-3-(2-bromopropionyl)-2-oxoimidazolidine-4-carboxylate (1) with sodium dimethyl malonate in HMPA at room temperature predominantly afforded tert-butyl (4S)-1-methyl-3-((2R)-2-methyl-3,3-bis(methoxycarbonyl)propionyl)-2-ox oimidazolidine-4-carboxylate ((S,R)-2a) in a good yield.
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