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  • Title: Stereoselective formation of N-acyliminium ion via chiral N,O-acetal TMS ether and its application to the synthesis of beta-amino acids.
    Author: Shin DY, Jung JK, Seo SY, Lee YS, Paek SM, Chung YK, Shin DM, Suh YG.
    Journal: Org Lett; 2003 Oct 02; 5(20):3635-8. PubMed ID: 14507191.
    Abstract:
    [reaction: see text] The highly stereoselective synthesis of beta-amino acids via the chiral 4-phenyloxazolidinone-controlled linear N-acyliminium ion reaction has been achieved by employing chiral N,O-acetal TMS ethers. In addition, the mechanism of the excellent stereochemical outcome has been elucidated. The oxazolidinone auxiliary plays a dual role in stereocontrol: the E/Z geometry control of the N-acyliminium ion induced by an initial stereoselective amide reduction, leading to the chiral N,O-acetal TMS ether, and face control of the nucleophile attack in the N-acyliminium ion reaction.
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