Trost, Barry M. et al. published their research in Journal of the American Chemical Society in 2001 | CAS: 174810-09-4

N,N’-((1R,2R)-Cyclohexane-1,2-diyl)bis(2-(diphenylphosphino)-1-naphthamide) (cas: 174810-09-4) belongs to chiral phosphine ligands. The synthesis of novel trialkylphosphines can be quite difficult, thereby limiting the scope of their chiral variants. Indeed, very little research on chiral tertiary phosphine-catalyzed asymmetric reactions occurred prior to the year 2000.HPLC of Formula: 174810-09-4

Geminal Dicarboxylates as Carbonyl Surrogates for Asymmetric Synthesis. Part I. Asymmetric Addition of Malonate Nucleophiles was written by Trost, Barry M.;Lee, Chul Bom. And the article was included in Journal of the American Chemical Society in 2001.HPLC of Formula: 174810-09-4 This article mentions the following:

Asym. alkylations of allylic geminal dicarboxylates with dialkyl malonates have been investigated. The requisite allylic geminal dicarboxylates are prepared in good yields and high isomeric purities either by ferric chloride-catalyzed addition of acid anhydrides to α,β-unsaturated aldehydes or by palladium-catalyzed isomerization and addition reactions of propargylic acetates with acetic acid. E.g., treatment of trans-cinnamaldehyde with 5 equivalent in the presence of 0.5% iron (III) chloride gave (E)-PhCH:CHCH(OAc)2 in 85% yield. E.g., treatment of (S)-MeCH[OSi(Ph)2CMe3]CCCH2OAc with 1.2 equivalent acetic acid and 1 mol% tetrakis(triphenylphosphine)palladium in toluene at 110° gave (E,S)-MeCH[OSi(Ph)2CMe3]CH:CCHCH(OAc)2 in 81% yield. The complex of di(allylchloropalladium) and nonracemic ligands derived from di(2-diphenylphosphinobenzoyl) amides of trans-1,2-diaminocyclohexane most efficiently catalyzed the asym. process to provide allylic carboxylate esters with high ee. E.g., sodium hydride was added to a solution of di-Me 2-methylmalonate and the mixture stirred at ambient temperature until gas evolution ceased; di(allylpalladium chloride), the (R,R)-trans-1,2-diaminocyclohexane di(2-diphenylphosphinobenzoyl) amide, and (E)-PhCH:CHCH(OAc)2 were added and the mixture was stirred for 2 h to give (R,E)-PhCH:CHCH(OAc)C(Me)(CO2Me)2 in 92% yield as a single regioisomer in >95% ee. By systematic optimization studies, factors affecting the enantioselectivity of the reaction have been probed. In general, higher ee’s have been achieved with those conditions which facilitate kinetic capture of the incipient π-allylpalladium intermediate. These conditions also proved effective for achieving high regioselectivities. The minor regioisomeric product was formed when reactive substrates or achiral ligands were employed for the reaction, and could be minimized through the use of the chiral ligand. Under the established conditions, the alkylation of various gem-dicarboxylates afforded monoalkylated products in high yields with greater than 90% ee. The process constitutes the equivalent of an addition of a stabilized nucleophile to a carbonyl group with high asym. induction. In the experiment, the researchers used many compounds, for example, N,N’-((1R,2R)-Cyclohexane-1,2-diyl)bis(2-(diphenylphosphino)-1-naphthamide) (cas: 174810-09-4HPLC of Formula: 174810-09-4).

N,N’-((1R,2R)-Cyclohexane-1,2-diyl)bis(2-(diphenylphosphino)-1-naphthamide) (cas: 174810-09-4) belongs to chiral phosphine ligands. The synthesis of novel trialkylphosphines can be quite difficult, thereby limiting the scope of their chiral variants. Indeed, very little research on chiral tertiary phosphine-catalyzed asymmetric reactions occurred prior to the year 2000.HPLC of Formula: 174810-09-4

Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis