Reaction of Triazolic Aldehydes with Diisopropyl Zinc: Chirality Dissipation versus Amplification

Abstract

The phenomenon of amplifying asymmetric autocatalysis (AAA) has recently been restricted to alkylation of several specific substrates with diisopropyl zinc (Soai reaction). Targeting the extension of the scope of this phenomenon, we studied the reaction of triazolic aldehydes with diisopropyl zinc. Experiments demonstrated a diversity of results for the dissipation of chirality, conserving the existent ee and spontaneous chirality generation. Computational analysis showed that depending on the level of oligomerization of the catalyst, one could expect amplification (monomeric catalyst) while maintaining the existing chirality (dimeric catalyst) or dissipation of chirality (tetrameric catalyst). These findings are promising for the elaboration of synthetic protocols controlling chirality generation. In addition, three optically active triazolic alcohols were characterized.

Keywords

• Soai reaction
• chirality amplification
• diisopropyl zinc
• DFT computations
• triazoles