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  • Title: Asymmetric synthesis of chloroisothreonine derivatives via syn-stereoselective Mannich-type additions across N-sulfinyl-α-chloroimines.
    Author: Callebaut G, Colpaert F, Nonn M, Kiss L, Sillanpää R, Törnroos KW, Fülöp F, De Kimpe N, Mangelinckx S.
    Journal: Org Biomol Chem; 2014 Jun 07; 12(21):3393-405. PubMed ID: 24740384.
    Abstract:
    Mannich-type reactions of O-Boc glycolic esters across chiral N-sulfinyl-α-chloroaldimines resulted in the efficient and syn-stereoselective synthesis of new γ-chloro-α-hydroxy-β-amino esters (dr > 99 : 1). The α-coordinating ability of the chlorine atom was of great importance for the diastereoselectivity of the Mannich-type reaction and overruled the chelation of the sulfinyl oxygen with the lithium ion of the incoming E-enolate in the transition state model. These novel chloroisothreonine derivatives proved to be excellent building blocks in asymmetric synthesis of novel syn-β,γ-aziridino-α-hydroxy esters and biologically relevant trans-oxazolidinone carboxylic esters.
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