85711-17-7Relevant articles and documents
Room temperature highly enantioselective nickel-catalyzed hydrovinylation
Lassauque, Nicolas,Francio, Giancarlo,Leitner, Walter
experimental part, p. 3133 - 3138 (2010/04/24)
At room temperature, nickel catalysts based on the new phosphoramidite (11bR)-N-[(S)-1-(naphthalen-1-yl)ethyl]-N-[(S)-1-(naphthalen-2-yl)ethyl] dinaphtho[2,1-d:1, 2'-f] [1,3,2]dioxaphosphepin-4-amine provide excellent selectivities for 3-arylbut-1-enes (9
Asymmetric cross-coupling of potassium 2-butenyltrifluoroborates with aryl and 1-alkenyl bromides catalyzed by a Pd(OAc)2/Josiphos complex
Yamamoto, Yasunori,Takada, Shingo,Miyaura, Norio
, p. 1368 - 1369 (2007/10/03)
The asymmetric cross-coupling reaction of [CH3CH= CHCH 2BF3]K with aryl or 1-alkenyl bromides selectively occurred at the γ-carbon of 2-butenylborane moiety with regioselectivities in a range of 84-99%. The enantioselectiv
Tunable phosphinite, phosphite and phosphoramidite ligands for the asymmetric hydrovinylation reactions
Park, Haengsoon,Kumareswaran, Ramaiah,RajanBabu
, p. 6352 - 6367 (2007/10/03)
Only a limited number of ligands have been successfully employed for the Ni-catalyzed asymmetric hydrovinylation reaction. Diarylphosphinites, carrying β-acylamino groups prepared from readily available carbohydrates, in conjunction with highly dissociated counteranions {[(3,5-(CF3) 2C6H3]4B- or SbF 6-}, effect the hydrovinylation of vinylarenes under ambient pressure of ethylene with high enantioselectivity. Nitrogen substituents such as -COCF3 and COPh groups lead to isomerization of the primary products (3-arylbutenes) to Z- and E-2-aryl-2-butenes. In a prototypical synthesis of a 2-arylproionic acid, (S)-3-(4-bromophenyl)-1-butene (89% ee) has be transformed into (R)-ibuprofen by Ni-catalyzed cross-coupling with i-BuMgBr, followed by oxidation of the double bond with NaIO4 and KMnO 4. Asymmetric codimerization of norbonene and ethylene using binaphthol-derived phosphoramidites as ligands gives 1:1, 2:1 or polymeric adducts depending on the relative configurations and nature of the BINAP and amine moieties. With one of the phosphoramidite-Ni complexes, counteranions BAr4- [Ar=3,5-(CF3)2C 6H3] and SbF6-, which had been used interchangeably in other reactions, give either a 1:1 adduct or a 2:1 adduct, respectively.