583960-72-9Relevant academic research and scientific papers
Room-temperature rhodium-catalyzed asymmetric 1,4-addition of potassium trifluoro(organo)borates
Gendrineau, Thomas,Genet, Jean-Pierre,Darses, Sylvain
supporting information; experimental part, p. 3486 - 3489 (2009/12/24)
For the first time the room-temperature rhodium-catalyzed asymmetric 1,4-addition of potassium aryltrifluoroborates to αβ-unsaturated substrates is described. Thanks to the use of a chiral diene as ligand for rhodium and triethylamine as base, to facilita
Chiral bis-phosphoramidites based on linked-BINOL for rhodium-catalyzed 1,4-addition of arylboronic acids to α,β-unsaturated carbonyl compounds
Yamamoto, Yasunori,Kurihara, Kazunori,Sugishita, Noriyuki,Oshita, Kengo,Piao, Dongguo,Miyaura, Norio
, p. 1224 - 1225 (2007/10/03)
Cationic rhodium(I) complex prepared from Shibasaki's linked-BINOL and [Rh(nbd)2]BF4 catalyzed asymmetric 1,4-addition of arylboronic acids to enones at room temperature with high enantioselectivities up to 99.8%ee. Copyright
Chiral [2.2.2] dienes as ligands for Rh(I) in conjugate additions of boronic acids to a wide range of acceptors
Defieber, Christian,Paquin, Jean-Francois,Serna, Sonia,Carreira, Erick M.
, p. 3873 - 3876 (2007/10/03)
We document a series of investigations that led to new substituted [2.2.2]-diene ligands which display high selectivity in Rh(I)-catalyzed conjugate addition reactions to substrates not previously examined with diene ligands. Moreover, we disclose an unexpected, interesting effect that results from the introduction of a third C=C onto the ligand scaffold (cf. 1).
Rhodium-catalyzed 1,4-addition of arylboronic acids to α,β-unsaturated carbonyl compounds: Large accelerating effects of bases and ligands
Itooka, Ryoh,Iguchi, Yuki,Miyaura, Norio
, p. 6000 - 6004 (2007/10/03)
The effects of ligands and bases in the rhodium(I)-catalyzed 1,4-addition of arylboronic acids to α,β-unsaturated carbonyl compounds were reinvestigated to carry out the reaction under mild conditions. Rhodium(I) complexes possessing a 1,5-cyclooctadiene (cod) and a hydroxo ligand such as [RhOH(cod)]2 exhibited excellent catalyst activities compared to those of the corresponding rhodium-acac or -chloro complexes and their phosphine derivatives. The reaction was further accelerated in the presence of KOH, thus allowing the 1,4-addition even at 0 °C. A cationic rhodium-(I)-(R)-binap complex, [Rh(R-binap)(nbd)]BF4, catalyzed the reaction at 25-50 °C in the presence of Et3N with high enantioselectivities of up to 99% ee for α,β-unsaturated ketones, 92% for aldehydes, 94% for esters, and 92% for amides.
