Synthesis of gamma,delta-unsaturated glycolic acids via sequenced brook and Ireland--claisen rearrangements.
Organozinc, -magnesium, and -lithium nucleophiles initiate a Brook/Ireland-Claisen rearrangement sequence of allylic silyl glyoxylates resulting in the formation of gamma,delta-unsaturated alpha-silyloxy acids.
Department of Chemistry, University of North Carolina at Chapel Hill, Chapel Hill, North Carolina 27599-3290, USA.
Daniel C
DC
Schmitt
Jeffrey S
JS
Johnson
D019281:Dimerization; D006016:Glycolates / Q000138:chemical synthesis* / Q000737:chemistry*; D006038:Glyoxylates / Q000737:chemistry
D006016:Glycolates; D006038:Glyoxylates; C031149:glycolic acid; C031150:glyoxylic acid