title: Asymmetric anti-aldol addition of achiral ketones via chiral N-amino cyclic carbamate hydrazones.
abstract: The asymmetric anti-aldol addition of ketone-derived donors and aldehyde acceptors is described. Asymmetric induction is achieved through the use of chiral N-amino cyclic carbamate (ACC) auxiliaries. The transformation exhibits essentially perfect anti-diastereoselectivity and enantioselectivity, and has the unusual feature of proceeding via thermodynamic, rather than kinetic control.
authors.affiliation: Department of Chemistry, University of Houston, Houston, Texas 77204-5003, USA.
authors.forename: John D
authors.initials: JD
authors.lastname: Knight
authors.forename: Don M
authors.initials: DM
authors.lastname: Coltart
mesh_terms: D000438:Alcohols / Q000138:chemical synthesis* / Q000737:chemistry; D000447:Aldehydes / Q000737:chemistry; D002219:Carbamates / Q000737:chemistry*; D006835:Hydrazones / Q000737:chemistry*; D007659:Ketones / Q000737:chemistry*; D007700:Kinetics; D015394:Molecular Structure; D013237:Stereoisomerism; D013816:Thermodynamics
chemical_list: D000438:Alcohols; D000447:Aldehydes; D002219:Carbamates; D006835:Hydrazones; D007659:Ketones