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.