title: tert-Butyldimethylsilyl-directed highly enantioselective approach to axially chiral α-allenols.
abstract: A highly efficient and enantioselective synthesis of axially chiral α-allenols was realized in practical yields with 96-99% ee or de from TBS-protected propargylic alcohols, aldehydes, and a commercially available, inexpensive, chiral, secondary amine (S)-α,α-diphenylprolinol or its enantiomer followed by desilylation. The easily removable TBS group not only acts as a protecting group, but also as a possible sterically directing group for the excellent enantioselectivity and in situ prevention of possible allene racemization.
authors.affiliation: State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences 345 Lingling Lu, Shanghai 200032, PR China.
authors.forename: Juntao
authors.initials: J
authors.lastname: Ye
authors.forename: Wu
authors.initials: W
authors.lastname: Fan
authors.forename: Shengming
authors.initials: S
authors.lastname: Ma
mesh_terms: D000475:Alkenes / Q000737:chemistry*; D012821:Silanes / Q000737:chemistry*; D013237:Stereoisomerism; D013379:Substrate Specificity
chemical_list: D000475:Alkenes; D012821:Silanes