830334-89-9Relevant academic research and scientific papers
Diastereoselective allylation of N-glyoxyloyl-(2R)-bornane-10,2-sultam and (1R)-8-phenylmenthyl glyoxylate: Synthesis of (2S,4S)-2-hydroxy-4-hydroxymethyl- 4-butanolide
Kiegiel, Katarzyna,Balakier, Tomasz,Kwiatkowski, Piotr,Jurczak, Janusz
, p. 3869 - 3878 (2004)
The diastereoselective addition of allylsilanes and allylstannanes to N-glyoxyloyl-(2R)-bornane-10,2-sultam 1 and (1R)-8-phenylmenthyl glyoxylate 7 in the presence of Lewis acids has been studied. We obtained diastereoselectivities up to 84% and 94% for the allylation of 2 and 7, respectively. The application of the allylation products of 1 or 2 in the synthesis of 4-butanolides, for example (2S,4S)-2-hydroxy-4-hydroxymethyl-4- butanolide 13 is presented.
