Tetrahedron letters

Straightforward entry to the pipecolic acid nucleus. Enantioselective synthesis of baikiain

X Ginesta, MA Pericas, A Riera

Index: Ginesta, Xavier; Pericas, Miquel A; Riera, Antoni Tetrahedron Letters, 2002 , vol. 43, # 5 p. 779 - 782

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Citation Number: 57

Abstract

New enantioselective syntheses of N-protected baikiain and pipecolic acid have been developed. The starting material is 2, 3-epoxy-5-hexen-1-ol (4) readily available in high ee by Sharpless epoxidation. The regio-and stereoselective epoxide ring-opening by allylamine afforded a doubly unsaturated amine that was converted into a carbamate (Boc) and submitted to ring-closing metathesis. The resulting cyclic amino diol 6 is a key ...