Density Functional Study of Organocatalytic Mannich-Type Reactions: Insight into Reverse Diastereoselectivities Arising from Catalysts with Different Scaffolds

摘要

Density functional study have been carried out to investigate the stereoselectivities in the Mannich-type reactions promoted by five typical amino acid catalysts with different scaffolds. The reverse diastereoselectivities in the cyclic and acyclic - and -amino acids-promoted Mannich reactions have been satisfactorily explained by the density functional theory (DFT) methods at the SMD/M06-2X/6-31G** computational level. The activation strain analysis has been used to account for the selectivity-switching for these selected bifunctional catalysts. (c) 2015 Wiley Periodicals, Inc.