1133149-34-4Relevant academic research and scientific papers
Mechanistic investigations of the Mukaiyama aldol reaction as a two part enantioselective reaction
Patel, Sachin G.,Wiskur, Sheryl L.
, p. 1164 - 1166 (2009)
Herein, we report a mechanistic investigation of an enantioselective tandem Mukaiyama aldol reaction, consisting of a carbon-carbon bond-forming reaction and a silylation protection step in which the enantioselectivity results exclusively from the silylation step. The reaction is carried out in the presence of a Lewis base paired with a chiral quarternary ammonium salt. Mechanistic studies indicate that the enantioselectivity of the silylation step is a kinetic resolution of the aldolate intermediate. The effects of sterics and electronics on the aldehyde starting material are also presented.
