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  • Title: Asymmetric synthesis of α-chloro-β-amino-N-sulfinyl imidates as chiral building blocks.
    Author: Colpaert F, Mangelinckx S, De Brabandere S, De Kimpe N.
    Journal: J Org Chem; 2011 Apr 01; 76(7):2204-13. PubMed ID: 21381724.
    Abstract:
    New chiral α-chloro-β-amino-N-sulfinyl imidates were synthesized in high yield and excellent diastereomeric excess via highly anti-selective Mannich-type reactions of (R(S))-methyl N-tert-butanesulfinyl-2-chloroethanimidate with aromatic aldimines. The α-chloro-β-amino-N-sulfinylimidates proved to be excellent building blocks for the asymmetric synthesis of β-amino-α-chloro amides and esters, aziridine-2-carboxylic amides and esters, trans-2-aryl-3-chloroazetidines, and methyl 4-phenyloxazolidin-2-one-5-carboxylate. The obtained absolute anti-diastereoselectivity is the opposite of the stereochemical outcome observed for α-methyl-substituted imidates.
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