Synthesis of enantiomerically pure ethylenediamines from chiral sulfinimines: a new twist to the Strecker reaction

Addition of various cyanide nucleophiles on chiral t-butylsulfinimine and p -tolylsulfinimine derivatives are described and demonstrated that aliphatic t-butylsulfinimines are excellent substrates for a new variant of the Stre cker reaction where cyanide ions are delivered through ethylisopropoxyalumi num cyanide or trimethylsilylcyanide combined with a Lewis acid catalyst. T he reaction proceeds with high yield and high diastereoselectivity, which c an be further improved by additional crystallizations. (C) 2001 Elsevier Sc ience Ltd. All rights reserved.