Journal of Organic Chemistry p. 6776 - 6784 (1995)
Update date:2022-08-05
Topics:
Kubota, Hitoshi
Kubo, Akira
Takahashi, Masami
Shimizu, Ryo
Da-te, Tadamasa
et al.
A novel type of stereospecific amination by dynamic kinetic resolution using (4S)-2-oxoimidazolidine-4-carboxylate (1) as a chiral auxiliary was developed. A reaction of a diastereomeric mixture of (4S)-3-<(2RS)-2-bromoacyl>-2-oxoimidazolidine-4-carboxylates 4 with an amine in the presence of a base in HMPA predominantly afforded (4S)-3-<(2R)-2-(alkylamino)acyl>-2-oxoimidazolidine-4-carboxylates (S,R)-7 in good yields.The reaction proceeded by stereospecific SN2 type amination incorporated with rapid interconversion between the substrates (S,S)-4 and (S,R)-4.Mechanistic study suggested that the unique stereoselectivity was induced through the interaction between an amine and the ester group of (S,S)-4 in the transition state.The chiral auxiliary was easily removed with alkoxide anion to afford the α-amino acid synthon in good yields.
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