406673-12-9Relevant academic research and scientific papers
Bismuth triflate-catalyzed addition of allylsilanes to N- alkoxycarbonylamino sulfones: Convenient access to 3-Cbz-protected cyclohexenylamines
Ollevier, Thierry,Li, Zhiya
supporting information; experimental part, p. 3251 - 3259 (2010/04/24)
Bismuth triflate was found to be an efficient catalyst in the Sakurai reaction of allyltrimethylsilanes with N-alkoxycarbonylamino sulfones. The reaction proceeded smoothly with a low catalyst loading of Bi(OTf) 3·4H2O (2-5 mol%) to afford the corresponding protected homoallylic amines in very good yields (up to 96%). A sequential allylation reaction followed by ring-closing metathesis delivers 6-8 membered 3-Cbz-protected cycloalkenylamines.
Highly diastereoselective synthesis of β-amino alcohols
Meester, Wim J.N.,Van Dijk, Rudmer,Van Maarseveen, Jan H.,Rutjes, Floris P.J.T.,Hermkens, Pedro H.H.,Hiemstra, Henk
, p. 2909 - 2911 (2007/10/03)
The highly diastereoselective synthesis of β-amino alcohols was presented. The several substituted β-amino alcohols were synthesized via a novel highly versatile intermediate, involving a combination of N-acyliminium ion and Weinreb amide chemistry. It was found that in the resulting five-membered ring, the allyl group blocks the top face of the molecule, thus forcing the incoming nucleophile to attack from the opposite side of the ring giving rise to the syn-β-amino alcohol as the main product.
