10.1021/jo801158g.s001 Aldo Peschiulli Aldo Peschiulli Cormac Quigley Cormac Quigley Seán Tallon Seán Tallon Yuri K. Gun’ko Yuri K. Gun’ko Stephen J. Connon Stephen J. Connon Organocatalytic Asymmetric Addition of Alcohols and Thiols to Activated Electrophiles: Efficient Dynamic Kinetic Resolution and Desymmetrization Protocols American Chemical Society 2008 Activated Electrophiles Efficient Dynamic Kinetic Resolution enantioselective desymmetrization Organocatalytic Asymmetric Addition DKR reactions catalyst azalactone steric bulk alcohol nucleophile acid residue 2008-08-15 00:00:00 Journal contribution https://acs.figshare.com/articles/journal_contribution/Organocatalytic_Asymmetric_Addition_of_Alcohols_and_Thiols_to_Activated_Electrophiles_Efficient_Dynamic_Kinetic_Resolution_and_Desymmetrization_Protocols/2920903 Bifunctional urea-based cinchona alkaloid derivatives have been shown to promote highly efficient DKR reactions of azalactones using an alcohol nucleophile. The optimum catalyst is remarkably insensitive to the steric bulk of the amino acid residue, allowing alanine-, methionine-, and phenylalanine-derived azalactones to undergo DKR with unprecedented levels of enantioselectivity using a synthetic catalyst. The first DKR of these substrates by thiols and the highly enantioselective desymmetrization of a <i>meso</i>-glutaric anhydride by thiolysis are also reported.