Electro‐Organic Stereoselective Dehydrogenative Homo‐Coupling of β‐Naphthylamines Derivatives

The electrochemical stereoselective dehydrogenative homocoupling of beta-naphthylamine derivatives was investigated and successfully accomplished, the chiral diaryl amines being obtained in up to 60 % yield. The use of an enantiopure beta-naphthylamine featuring an aminoalcohol as chiral auxiliary led to the expected 2,2'-binaphthyl diamine derivative in up to 96/4 diastereoisomeric ratio. The application of the methodology to the intramolecular cross coupling of the enantiopure bis-N-beta-naphthylamine 1,2-trans-diamino cyclohexane led to the formation of a single enantiopure diastereoisomer in 37 % yield.The electrochemical stereoselective dehydrogenative homocoupling of enantiopure beta-naphthylamines featuring an aminoalcohol as chiral auxiliary led to the chiral 2,2'-binaphthyl diamine derivatives in up to 60 % yield and 96/4 diastereoisomeric ratio. image