title: Stereochemical diversity in chiral ligand design: discovery and optimization of catalysts for the enantioselective addition of allylic halides to aldehydes.
abstract: [reaction: see text] We have identified a new set of stereochemically diverse oxazoline ligands derived from simple amino acids that promote the Cr-catalyzed enantioselective addition of allylic halides to aldehydes in up to 95% ee. The Cr-catalyzed allylation using ligand 1d is rather insensitive to the nature of the allylic bromide (crotyl, allyl, and methallyl) in that >90% ee is observed for all three bromides evaluated in the addition to benzaldehyde.
authors.affiliation: Department of Chemistry, University of Utah, 315 South 1400 East, Salt Lake City, Utah 84112-085, USA.
authors.forename: Jae-Young
authors.initials: JY
authors.lastname: Lee
authors.forename: Jeremie J
authors.initials: JJ
authors.lastname: Miller
authors.forename: Steven S
authors.initials: SS
authors.lastname: Hamilton
authors.forename: Matthew S
authors.initials: MS
authors.lastname: Sigman
mesh_terms: D000447:Aldehydes / Q000032:analysis / Q000138:chemical synthesis / Q000737:chemistry*; D000596:Amino Acids / Q000737:chemistry*; D002384:Catalysis; D002857:Chromium / Q000737:chemistry; D006846:Hydrocarbons, Halogenated / Q000737:chemistry*; D010080:Oxazoles / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000447:Aldehydes; D000596:Amino Acids; D006846:Hydrocarbons, Halogenated; D010080:Oxazoles; D002857:Chromium