Enantioselective Amination of Silylketene Acetals with (N‐Arylsulfonylimino)phenyliodinanes Catalyzed by Chiral Dirhodium(II) Carboxylates: Asymmetric Synthesis of Phenylglycine Derivatives.

Abstract The first catalytic enantioselective amination of silylketene acetals with ( N -arylsulfonylimino)phenyliodinanes is described. The reaction of silylketene acetals derived from methyl phenylacetates with [ N -(2-nitrophenylsulfonyl)imino]phenyliodinane (NsN = IPh) under the catalysis of dirhodium(II) tetrakis[ N -tetrachlorophthaloyl-( S )- tert -leucinate], Rh 2 ( S -TCPTTL) 4 , proceeds in benzene at room temperature to give N -(2-nitrophenylsulfonyl)phenylglycine derivatives in high yields and with enantioselectivities of up to 99% ee.