title: Diastereoselective synthesis of vicinal tertiary diols.
abstract: A strategy for the synthesis of differentiated vicinal tertiary diols is described. The key step is a high-yielding, diastereoselective LaCl3·2LiCl-mediated addition of a Grignard or organolithium reagent to ketone 2a. The reaction is believed to proceed via a 1,3-chelated intermediate. One of the adducts has been transformed into a functionalized cyclopentenone resembling the core structure of pactamycin.
authors.affiliation: Department of Chemistry and Biochemistry, Brigham Young University, Provo, Utah 84602, United States.
authors.forename: Brad M
authors.initials: BM
authors.lastname: Loertscher
authors.forename: Phil R
authors.initials: PR
authors.lastname: Young
authors.forename: Patrick R
authors.initials: PR
authors.lastname: Evans
authors.forename: Steven L
authors.initials: SL
authors.lastname: Castle
mesh_terms: D000438:Alcohols / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D003517:Cyclopentanes / Q000138:chemical synthesis / Q000737:chemistry; D007659:Ketones / Q000737:chemistry; D015394:Molecular Structure; D010142:Pactamycin / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000438:Alcohols; D003517:Cyclopentanes; D007659:Ketones; D010142:Pactamycin; C013905:cyclopentenone