Tetrahedron

Auxiliary controlled enantioselective synthesis of 3-aryl-prolines

S Laabs, W Münch, JW Bats, U Nubbemeyer

Index: Laabs, Stephan; Muench, Winfried; Bats, Jan W; Nubbemeyer, Udo Tetrahedron, 2002 , vol. 58, # 7 p. 1317 - 1334

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Citation Number: 34

Abstract

The synthesis of optically active cis 3-aryl proline derivatives was achieved in a five-step sequence involving an enantioselective aza-Claisen rearrangement as the key step. Initially, suitable cinnamyl amines were generated via a Pd (0) catalyzed amination of the corresponding N-allyl mesylates using optically active proline derivatives as chiral auxiliaries. The zwitterionic aza-Claisen rearrangement with azidoacetyl fluoride gave the ...