Synthesis of chiral N-protected 1,2-dihydro-quinoline-2-carbonitrile and 1,2-dihydro-isoquinoline-1-carbonitrile via an asymmetric Reissert reaction

Addition of cyanide ion to chiral N-acyl-quinolinium and N-acyl-isoquinolinium salts led selectively to 1,2-addition products. Removal of the chiral auxiliary affords the title compounds in pure enantiomeric form. (c) 2005 Elsevier Ltd. All rights reserved.