Fitness of driving force and catalytic space in chiral catalyst design. Application of axial biscarboline N–O chiral catalyst for enantioselective allylation of allyltrichlorosilane to bulky substituted aldehydes

Abstract The relationship between a catalyst and its catalytic substrate was proposed based on our early and current study. This is figuratively summarized as the fitness of (1) driving force and (2) catalytic space. This assumption was examined in allylations of various aldehydes with different substituents, which were synthesized from tryptophan methyl ester via four reaction steps in high yields. High up to 96%ee was achieved in the allylations. The assumptions initially were confirmed to agree with the experimental results well.