ENANTIOSELEKTIVE KATALYSE, 89AZYKLISCHE UND MAKROZYKLISCHE BINAPHTHYLDERIVATE

Abstract

Abstract A new synthesis of 3,3′‐diformyl‐2,2′‐dihydroxy‐1,1′‐binaphthyl 1 is described. The macrocyclic compound 3 is formed by Schiff base condensation of two moles of 1 with two moles of (R,R)‐1,2‐Diamino‐1,2‐diphenylethane RR‐2 . Reduction of 3 yields the macrocycle 7 . The binaphthylketones S‐13 ‐ S‐15 are synthesised starting from (S)‐3,3′‐dicarboxy‐2,2′‐dihydroxy‐1,1′‐binaphthyl S‐16 which is reacted with the corresponding Li‐organic compound. By Schiff base condensation of S‐13 ‐ S‐15 with (R)‐ and (S)‐1‐amino‐1‐phenylethane the new imines 16 ‐ 21 are prepared. The compounds 3 and 16 ‐ 20 are used as optically active ligands in the copper(II)‐catalysed enantioselective cyclopropanation of styrene with ethyl diazoacetate. The product ethyl cis/trans‐2‐phenylcyclopropanecarboxylate is obtained with an optical induction up to 36.6%.