title: Enantio- and diastereoselective synthesis of syn-β-hydroxy-α-vinyl carboxylic esters via reductive aldol reactions of ethyl allenecarboxylate with 10-TMS-9-Borabicyclo[3.3.2]decane and DFT analysis of the hydroboration pathway.
abstract: An enantio- and diastereoselective synthesis of syn-β-hydroxy-α-vinyl carboxylate esters 3 via the reductive aldol reaction of ethyl allenecarboxylate (2) with 10-trimethylsilyl-9-borabicyclo[3.3.2]decane (1R) has been developed. Density functional theory calculations suggest that the allene hydroboration involves the 1,4-reduction of 2 with the 1R, leading directly to dienolborinate Z-(O)-8a.
authors.affiliation: Department of Chemistry, Scripps Florida , Jupiter, Florida 33458, United States, and Department of Chemistry and Biochemistry, Brigham Young University , Provo, Utah 84602, United States.
authors.forename: Jeremy
authors.initials: J
authors.lastname: Kister
authors.forename: Daniel H
authors.initials: DH
authors.lastname: Ess
authors.forename: William R
authors.initials: WR
authors.lastname: Roush
mesh_terms: D001896:Boron Compounds / Q000737:chemistry*; D001643:Bridged Bicyclo Compounds / Q000737:chemistry*; D002264:Carboxylic Acids / Q000737:chemistry*; D004952:Esters; D015394:Molecular Structure; D013237:Stereoisomerism; D014297:Trimethylsilyl Compounds / Q000737:chemistry*; D014753:Vinyl Compounds / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: C546486:10-R-9-borabicyclo(3.3.2)decane; C588043:10-trimethylsilyl-9-borabicyclo(3.3.2)decane; D001896:Boron Compounds; D001643:Bridged Bicyclo Compounds; D002264:Carboxylic Acids; D004952:Esters; D014297:Trimethylsilyl Compounds; D014753:Vinyl Compounds