Tetrahedron Letters

A convenient allylsilane-N-acyliminium route toward 5-alkylindolizidines. Diastereoselective synthesis of (±)-indolizidine 167B

S Peroche, R Remuson, Y Gelas-Mialhe, JC Gramain

Index: Peroche, Sandrine; Remuson, Roland; Gelas-Mialhe, Yvonne; Gramain, Jean-Claude Tetrahedron Letters, 2001 , vol. 42, # 28 p. 4617 - 4619

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Citation Number: 26

Abstract

The allylsilyl functional group is a weak carbon nucleophile extensively used for trapping N-acyliminium ions, thus providing an exceptionally useful method for carboncarbon bond formation in both intermolecular and intramolecular cases. 4 We have applied the intramolecular methodology toward the synthesis of quinolizidine and indolizidine alkaloids. 5., 6. and 7. In this article, we describe an intermolecular reaction between the allylsilyl functional group of homoallylic ...