Journal
TETRAHEDRON
Volume 62, Issue 26, Pages 6312-6320Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2006.04.065
Keywords
thiolactams; thioiminium salts; lithium acetylides; Grignard reagents; 2,2-disubstituted cyclic amines; silylcarbocyclization
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The reaction of thioiminium salts derived from gamma- and delta-thiolactams with lithium acetylides and Grignard reagents proceeded sequentially to give 2,2-disubstituted pyrrolidines and piperidines in moderate to high yields. In the initial step of the reaction, 2-(methylthio)pyrrolidines and -piperidines may be formed. The use of lithium (trimethylsilyl)acetylide gave the products most effectively. Aryl-, alkyl-, and allylmagnesium halides were used as Grignard reagents. Silylcarbocyclization of N-allyl 2-ethynyl cyclic amines with HSiMe2Ph in the presence of a catalytic amount of Rh-4(CO)(12) was carried out to give trisubstituted hexahydro-1H-pyrrolizines and octahydroindolizines. (c) 2006 Elsevier Ltd. All rights reserved.
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