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An efficient C2-homologation of aromatic aldehydes via 5-hydroxyisoxazolidines
Di Nunno,Scilimati
, p. 4121 - 4132 (2007/10/02)
The reaction of lithium enolate of acetaldehyde (generated by the known cycloreversion of THF in the presence of n-BuLi) with a number of aryl N-phenylnitrones affords 2-phenyl-3-aryl-5-hydroxyisoxazolidines (trans + cis) in high yields. A low conversion or no reaction at all were instead observed with some N-alkylnitrones (methyl and t-butyl, respectively). Base (or acid) induced decomposition of 5-hydroxyisoxazolidines allows cinnamaldehydes to be obtained in high yields. Thus the combination of the synthesis and decomposition of 5-hydroxyisoxazolidines provides a new efficient way for the C2-homologation of aromatic aldehydes.
