Ester-enolate Claisen rearrangement of proline-containing α-acyloxy-α-vinylsilane. Synthesis of pyrrolidine-fused glutamate analogs

K Sakaguchi, M Yamamoto, Y Watanabe, Y Ohfune

Index: Sakaguchi, Kazuhiko; Yamamoto, Masahiro; Watanabe, Yusuke; Ohfune, Yasufumi Tetrahedron Letters, 2007 , vol. 48, # 28 p. 4821 - 4824

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Citation Number: 17

Abstract

The stereoselective syntheses of pyrrolidine-fused aspartate and glutamate analogs,(S)-α- carboxymethyl-proline 3 and (S)-α-2-carboxyethyl-proline 4, using a chirality-transferring ester-enolate Claisen rearrangement of α-vinyl-α-acyloxysilane having a Boc-Pro as an acyloxy group, are described. The stereochemical outcome of the proline ester-derived ester- enolate Claisen rearrangement is also disclosed.