Asymmetric Synthesis XI: Stereoselective Synthesis of α-Alkyl-2-Furfurylamines Via d-Camphor Ketimine Intermediate

Abstract

(R)-α-alkyl-2-furfurylamines (7), ranging from 5–67%d.e., are obtained by asymmetric alkylation of d-camphor ketimine (3). Using 1,3-diiodopropane and dibromoxylene as alkylating reagents, diimine derivatives (6f) and (6g) are formed. However, 1,2-dibromoethane gives coupling product (6h).