title: Lithium amidoborane, a highly chemoselective reagent for the reduction of α,β-unsaturated ketones to allylic alcohols.
abstract: Lithium amidoborane (LiNH(2)BH(3), LiAB for short), is capable of chemoselectively reducing α,β-unsaturated ketones to the corresponding allylic alcohols at ambient temperature. A mechanistic study shows that the reduction is via a double hydrogen transfer process. The protic H(N) and hydridic H(B) in amidoborane add to the O and C sites of the carbonyl group, respectively.
authors.affiliation: National University of Singapore, Singapore.
authors.forename: Weiliang
authors.initials: W
authors.lastname: Xu
authors.forename: Yonggui
authors.initials: Y
authors.lastname: Zhou
authors.forename: Ruimin
authors.initials: R
authors.lastname: Wang
authors.forename: Guotao
authors.initials: G
authors.lastname: Wu
authors.forename: Ping
authors.initials: P
authors.lastname: Chen
mesh_terms: D001880:Boranes / Q000737:chemistry*; D007659:Ketones / Q000737:chemistry*; D018020:Lithium Compounds / Q000737:chemistry*; D015394:Molecular Structure; D009943:Organophosphorus Compounds / Q000737:chemistry*; D010084:Oxidation-Reduction; D020005:Propanols / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D001880:Boranes; D007659:Ketones; D018020:Lithium Compounds; D009943:Organophosphorus Compounds; D020005:Propanols; C571211:lithium amidoborane; C006463:allyl alcohol