51577-40-3Relevant articles and documents
Copper-catalyzed asymmetric conjugate addition with chiral SimplePhos ligands
Palais, Laetitia,Alexakis, Alexandre
supporting information; experimental part, p. 10473 - 10485 (2010/05/02)
SimplePhos ligands represent a novel class of monodentate chiral ligands based on a chiral amine moiety and flexible diaryl groups on the phosphorous atom. They can be easily prepared by two different pathways and they can be highly functionalised. Herein we report the copper-catalysed asymmetric conjugate addition of diethyl zinc and trialkylaluminium reagents with SimplePhos ligands, which gives high enantioselectivity with cyclic enones, acyclic enones and nitro-olefins, with up to 98.6 % ee. Of particular interest is the reaction of trialkylaluminium reagents with a wide range of 3substituted enones, thus allowing the formation of stereogenic quaternary carbon centres.
Synthesis of carbocycles via intramolecular conjugate additions: Total syntheses of axane sesquiterpenoids
Guevel, Alyx-Caroline,Hart, David J.
, p. 473 - 479 (2007/10/02)
Syntheses of (±)-axamide-1 (2) and (±)-axisonitrile-1 (1) are described. The syntheses require 12 steps and 13 steps, respectively, from vinylogous ester 8 and feature the diastereoselective cyclization of unsaturated ester 7 to perhydroindan 5. Some interesting reactions of the organometallic derived from [(trimethylsilyl)methyl]magnesium chloride and cerium trichloride are also described.
