162291-02-3 Usage
Reactions
Ferrocenylphosphine ligands of the type cpFecp(PR2)(*CH(CH3)PR'2) are a class of asymmetric ligands developed at Solvias in Basel, Switzerland. Ligands of this type are currently used industrially in the stereoselective synthesis of commercial products. A unique feature of these bidentate ligands is the presence of a fixed phosphine moiety and a stereogenic,functionalized side chain, which can be easily modified to accommodate electronic and steric requirements. Based on a versatile synthetic procedure starting with optically active ferrocenes of the type cpFecp(PR2)(*CH(CH3)X) [X = OAc or NR2], a variety of donor atoms can be introduced into the side chain.4 These ferrocene based phosphine ligands have wide application in the stereoselective hydrogenation of substituted acetamidoacrylates, enol acetates, β-ketoesters and simple alkenes.
Pd-catalyzed, enantioselective, intramolecular α-substituted cyclic ketones: facile synthesis of functionalized chiral spirobicycles.
Asymmetric boron conjugate addition of α,β-unsaturated carbonyl compounds catalyzed by
CuOTf/Josiphos under non-alkaline conditions.
Chiral amides via copper-catalyzed enantioselective conjugate addition.
Ruthenium-catalyzed enantioselective synthesis of β-amino alcohols from 1,2-diols by “borrowing hydrogen”.
Cobalt-catalyzed asymmetric addition of silylacetylenes to 1,1-disubstituted allenes.
Chemical Properties
Dark orange powder
General Description
sold in collaboration with Solvias AG
Check Digit Verification of cas no
The CAS Registry Mumber 162291-02-3 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,6,2,2,9 and 1 respectively; the second part has 2 digits, 0 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 162291-02:
(8*1)+(7*6)+(6*2)+(5*2)+(4*9)+(3*1)+(2*0)+(1*2)=113
113 % 10 = 3
So 162291-02-3 is a valid CAS Registry Number.
InChI:InChI=1/C31H39P2.C5H5.Fe/c1-25(32(26-15-6-2-7-16-26)27-17-8-3-9-18-27)30-23-14-24-31(30)33(28-19-10-4-11-20-28)29-21-12-5-13-22-29;1-2-4-5-3-1;/h4-5,10-14,19-27H,2-3,6-9,15-18H2,1H3;1-5H;/t25-;;/m0../s1
162291-02-3Relevant articles and documents
Asymmetric Hydrogenation of Aryl Perfluoroalkyl Ketones Catalyzed by Rhodium(III) Monohydride Complexes Bearing Josiphos Ligands
Brüning, Fabian,Nagae, Haruki,K?ch, Daniel,Mashima, Kazushi,Togni, Antonio
supporting information, p. 10818 - 10822 (2019/07/31)
The asymmetric hydrogenation of 2,2,2-trifluoroacetophenones and aryl perfluoroalkyl ketones was developed using a unique, well-defined chloride-bridged dinuclear rhodium(III) complex bearing Josiphos-type diphosphine ligands. These complexes were prepared from [RhCl(cod)]2, Josiphos ligands, and hydrochloric acid. As catalyst precursors, they allow for the efficient and enantioselective synthesis (up to 99 % ee) of chiral secondary alcohols with perfluoroalkyl groups. This system does not require an activating base for the hydrogenation of 2,2,2-trifluoroacetophenones. Additionally, the enantioselective C=O hydrogenations of 2-phenyl-3-(haloacetyl)-indoles, a class of privileged structures in medicinal chemistry, is reported for the first time.