Stereoselective Synthesis of α,β-Diamino Nitriles from Amino Acids
- 1 January 1994
- journal article
- research article
- Published by Georg Thieme Verlag KG in Synthesis
- Vol. 1994 (07) , 733-738
- https://doi.org/10.1055/s-1994-25559
Abstract
α-Amino acids 1 are readily converted into the corresponding N, N-dibenzylamino aldehydes 2 which in turn serve as starting materials for enantiomerically pure α- N,N-dibenzylamino aldimines 5, 6 and 7 having benzyl, tosyl and trimethylsilyl groups, respectively, at the aldimine nitrogen atom. All three classes of chiral aldimines undergo stereoselective Lewis acid promoted Me3SiCN addition reactions with non-chelation controlled formation of the corresponding α,β-diamino nitriles. All of the reaction sequences occur without any racemization.Keywords
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