Synthesis of 2-azaspiro[4.4]nonan-1-ones via phosphine-catalysed [3+2]-cycloadditions
作者： Sarah R. Yong , Morwenna C. Williams , Stephen G. Pyne , Alison T. Ung , Brian W. Skelton
DOI: 10.1016/J.TET.2005.06.050
关键词: Organic chemistry 、 Ethyl ester 、 Acid hydrolysis 、 Acrylate 、 Amide 、 Phosphine 、 Chemistry 、 Derivative (chemistry) 、 Curtius rearrangement 、 Camphor
摘要: Abstract The phosphine-catalyzed [3+2]-cycloaddition of the 2-methylene γ-lactams 4 and 5 acrylate 6 with ylides derived from ethyl ester, amide or chiral camphor sultam derivative 2-butynoic acid ( 7a–c ) give directly, indirectly after reductive cyclization, spiro-heterocyclic products. 32 underwent Curtius rearrangement then hydrolysis to two novel spiro-cyclic ketones, 41 42 .
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