82234-81-9Relevant articles and documents
Carbenoid insertion into alkenylzirconocenes - A convergent synthesis of functionalised allylmetallics
Kasatkin,Whitby
, p. 6211 - 6216 (2000)
Insertion of lithium alkylcarbenoids RC(A)LiX, A = CN, P(O)(OEt)2, SO2Ph, OMe into alkenylzirconocene chlorides derived by hydrozirconation of terminal alkynes affords functionalised allylzirconium reagents which may be further elaborated. (C) 2000 Elsevuer Science Ltd.
Direct substitution of primary allylic amines with sulfinate salts
Wu, Xue-Song,Chen, Yan,Li, Man-Bo,Zhou, Meng-Guang,Tian, Shi-Kai
supporting information, p. 14694 - 14697 (2012/11/07)
The NH2 group in primary allylic amines was substituted directly by sulfinate salts with excellent regio- and stereoselectivities. In the presence of 0.1 mol % [Pd(allyl)Cl]2, 0.4 mol % 1,4- bis(diphenylphosphino)butane (dppb), and excess boric acid, a range of α-unbranched primary allylic amines were smoothly substituted with sodium sulfinates in an α-selective fashion to give structurally diverse allylic sulfones in good to excellent yields with exclusive E selectivity. Replacing dppb with 1,1′-bi-2-naphthol (BINOL) allowed unsymmetric α-chiral primary allylic amines to be transformed into the corresponding allylic sulfones in good to excellent yields with excellent retention of ee. Importantly, the reaction complements known asymmetric methods in substrate scope via its unique ability to provide α-chiral allylic sulfones with high optical purity starting from unsymmetric allylic electrophiles.