✍ Scribed by Florence Roger; Marie-Gabrielle Le Pironnec; Michel Guerro; Patrick Gougeon; Philippe Gall; Philippe Le Grel; Michele Baudy-Floc'h
No coin nor oath required. For personal study only.
Diastereoselective Synthesis of N-(α-Aryl-α-haloacetyl) Amino Acid Esters by Acylation Using 3-Aryl-2,2-dicyanooxiranes.
-α-Arylα-bromo ketenes are generated in situ starting from epoxides (I) by treatment with Li 2 NiBr 4 , followed by the addition of Et 3 N at -78 • C. Trapping of these intermediates with chiral amino esters gives the hitherto unknown optically active title amino acid esters in a diastereoselective manner. It is found that the (S)-amino esters can induce (R)-configuration and (R)-amino ester the (S)-configuration at the new chiral center. -(ROGER, FLORENCE;
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