title: Enantioselective syntheses of syn- and anti-β-hydroxyallylsilanes via allene hydroboration-aldehyde allylboration reactions.
abstract: The kinetic hydroboration of allenylsilane 5 with ((d)Ipc)(2)BH at -40 °C provides allylborane 9Z with ≥12:1 selectivity. When the hydroboration is performed at temperatures above -40 °C, 9Z isomerizes to the thermodynamically more stable allylborane 9E with >20:1 selectivity. Subsequent treatment of 9Z or 9E with aldehydes at -78 °C provides syn- or anti-β-hydroxyallylsilanes, 7 or 8, respectively.
authors.affiliation: Department of Chemistry, Scripps Florida, Jupiter, Florida 33458, USA.
authors.forename: Ming
authors.initials: M
authors.lastname: Chen
authors.forename: William R
authors.initials: WR
authors.lastname: Roush
mesh_terms: D000447:Aldehydes / Q000737:chemistry*; D000466:Alkadienes / Q000737:chemistry*; D000475:Alkenes / Q000737:chemistry*; D001895:Boron / Q000737:chemistry*; D006900:Hydroxylation; D007700:Kinetics; D015394:Molecular Structure; D012821:Silanes / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000447:Aldehydes; D000466:Alkadienes; D000475:Alkenes; D012821:Silanes; C511847:allylsilane; C025947:propadiene; D001895:Boron