Diastereoselective alkylation of the dianion of 5-ethoxy-4 (S)-hydroxy-1-isopropyl-2-pyrrolidinone; Synthesis of enantiomerically pure azabicycles

WJ Klaver, H Hiemstra, WN Speckamp

Index: Klaver, Wim J.; Hiemstra, Henk; Speckamp, Nico Tetrahedron Letters, 1987 , vol. 28, # 14 p. 1581 - 1584

Full Text: HTML

Citation Number: 21

Abstract

Abstract: The alkylation of the dianion of the title compound (2), readily prepared from (S)- malic acid, with w-iodo-l-trimethylsilyl-2-alkynes (8a-c) occurs with high trans-selectivity with respect to the hydroxyl function. The productsTITa-c) cyclize in formic acid to enantiomerically pure azabicyclic allenes (12a-c), one of wah-(12b) might be a suitable precursor to peduncularine (15).