Stereoselective and catalytic synthesis of anti-β-Alkoxy-α-azido carboxylic derivatives

Direct addition of a chiral N-azidoacetyl thiazolidinethione to a variety of dialkyl acetals catalyzed by a commercially available and structurally simple nickel(II) complex gives access in good yields and a highly stereocontrolled manner to anti-beta-alkoxy-alpha-azido carboxylic derivatives which, in turn, can be easily converted into a wide array of enantiomerically pure compounds

Stereoselective alkylation of (S)-N-acyl-4-isopropyl-1,3-thiazolidine-2-thiones catalyzed by (Me3P)2NiCl2

The structurally simple (Me3P)2NiCl2 complex catalyzes SN1-type alkylations of chiral N-acyl thiazolidinethiones with diarylmethyl methyl ethers and other stable carbenium cations. The former can contain a variety of functional groups and heteroatoms at the α-position. The resultant adducts are isolated as single diastereomers in high yields and can be converted into enantiomerically pure derivatives in a straightforward manner

Stereoselective synthesis of protected peptides containing an anti β‐Hydroxy tyrosine

Protected peptides containing an anti b-hydroxy tyrosine are synthesized in a straightforward and highly efficient manner through the direct and stereoselective addition of N-azidoacetyl-4-isopropyl-1,3-thiazolidine-2-thione to dialkyl acetals catalyzed by a nickel(II) complex, the forging of an amide bond by removal of the chiral auxiliary with an amino ester, and final coupling with a third amino acid

Stereoselective and catalytic synthesis of anti-β-Alkoxy-α-azido carboxylic derivatives

Direct addition of a chiral N-azidoacetyl thiazolidinethione to a variety of dialkyl acetals catalyzed by a commercially available and structurally simple nickel(II) complex gives access in good yields and a highly stereocontrolled manner to anti-beta-alkoxy-alpha-azido carboxylic derivatives which, in turn, can be easily converted into a wide array of enantiomerically pure compounds