0000000001302916
AUTHOR
Filip Colpaert
Asymmetric synthesis of chloroisothreonine derivatives via syn-stereoselective Mannich-type additions across N-sulfinyl-α- chloroimines
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.
CCDC 977961: Experimental Crystal Structure Determination
Related Article: Gert Callebaut, Filip Colpaert, Melinda Nonn, Loránd Kiss, Reijo Sillanpää, Karl W. Törnroos, Ferenc Fülöp, Norbert De Kimpe, Sven Mangelinckx|2014|Org.Biomol.Chem.|12|3393|doi:10.1039/C4OB00243A
CCDC 977962: Experimental Crystal Structure Determination
Related Article: Gert Callebaut, Filip Colpaert, Melinda Nonn, Loránd Kiss, Reijo Sillanpää, Karl W. Törnroos, Ferenc Fülöp, Norbert De Kimpe, Sven Mangelinckx|2014|Org.Biomol.Chem.|12|3393|doi:10.1039/C4OB00243A
CCDC 977960: Experimental Crystal Structure Determination
Related Article: Gert Callebaut, Filip Colpaert, Melinda Nonn, Loránd Kiss, Reijo Sillanpää, Karl W. Törnroos, Ferenc Fülöp, Norbert De Kimpe, Sven Mangelinckx|2014|Org.Biomol.Chem.|12|3393|doi:10.1039/C4OB00243A