Methodologies for the Dynamic Kinetic Diastereoselective Acylation (DKDA) of Lactols• The synthesis of rare and unnatural sugars has frustrated chemists for decades. Acylated Achmatowicz derived lactols have been used for the de novo synthesis of rare sugars since 2003, but the acylation step has always been unselective.• Developed a DKDA for the acylation of Achmatowicz derived lactols.• Demonstrated the utility of the DKDA by developing a novel route to all eight possible stereo-isomers of 2,3,4,6-tetradeoxy-4-amino sugars where all three stereo-centers are controlled independently by chiral catalysts.• Expanded the scope of the dynamic kinetic stereoselective acylation to 2-chromanols.Site-Selective Functionalization Reactions for Carbohydrates• The site-selective functionalization of carbohydrate hydroxyls is one of the long-standing challenges in organic chemistry. • Developed an innovative site-selective acylation reaction for carbohydrate trans diols using a pair of chiral catalysts. • Devised a selectivity model based on a novel cation-n interaction. Verified the cation-n interaction using DFT calculations in collaboration with Peng Liu’s lab at the University of Pittsburgh.• Currently developing a small molecule catalyzed site-selective phosphoramidation reaction for carbohydrate trans diols.