title: Transfer of axial chirality through the nickel-catalysed hydrocyanation of chiral allenes.
abstract: The transfer of axial chirality of allenes is beginning to be exploited as a powerful method for creating central chirality, particularly through the use of transition metal catalysis. In this communication, the transfer of axial chirality of chiral allenes via nickel-catalysed hydrocyanation is achieved through both regio- and face-selective hydronickelation as well as regioselective reductive elimination. This protocol was applied to 12 substrates and gave chiral carbonitriles with up to 97% ee. Further application to hydrocyanative cyclization using a chiral allene-yne is also presented, along with a discussion of the corresponding mechanism of racemization.
authors.affiliation: Graduate School of Pharmaceutical Sciences, Chiba University, 1-8-1 Inohana, Chuo-ku, Chiba, Japan. araisgr@chiba-u.jp.
authors.forename: Yuka
authors.initials: Y
authors.lastname: Amako
authors.forename: Shigeru
authors.initials: S
authors.lastname: Arai
authors.forename: Atsushi
authors.initials: A
authors.lastname: Nishida