Organocatalytic asymmetric addition of alcohols and thiols to activated electrophiles: efficient dynamic kinetic resolution and desymmetrization protocols.
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 meso-glutaric anhydride by thiolysis are also reported.
Peschiulli
Aldo
A
Centre for Synthesis and Chemical Biology, School of Chemistry, University of Dublin, Trinity College, Dublin 2, Ireland.
Quigley
Cormac
C
Tallon
Seán
S
Gun'ko
Yuri K
YK
Connon
Stephen J
SJ
D000409:Alanine / Q000031:analogs & derivatives / Q000737:chemistry; D000438:Alcohols / Q000737:chemistry*; D000596:Amino Acids / Q000737:chemistry*; D000812:Anhydrides / Q000737:chemistry; D002930:Cinchona Alkaloids / Q000737:chemistry*; D007700:Kinetics; D007783:Lactones / Q000737:chemistry*; D020005:Propanols / Q000737:chemistry; D013438:Sulfhydryl Compounds / Q000737:chemistry*; D014508:Urea / Q000031:analogs & derivatives; D014633:Valine / Q000031:analogs & derivatives
D000438:Alcohols; D000596:Amino Acids; D000812:Anhydrides; D002930:Cinchona Alkaloids; D007783:Lactones; D020005:Propanols; D013438:Sulfhydryl Compounds; C047207:N-benzoylalanine; C006463:allyl alcohol; D014508:Urea; D014633:Valine; D000409:Alanine