Iron-catalyzed olefin carbometalation was written by Nakamura, Masaharu;Hirai, Atsushi;Nakamura, Eiichi. And the article was included in Journal of the American Chemical Society in 2000.Reference of 55700-44-2 This article mentions the following:
Iron catalysts, involving a new (soft)phosphine/(hard)diamine ligand system for a iron/zinc bimetallic reagent, are effective for promotion of olefin enantioselective carbometalation. Thus, treatment of the cyclopropenone acetal I with RMgBr (R = Ph, allyl, Me, PhCH2CH2) or R2Zn (R1 = Et, pentyl) in THF containing FeCl3 and subsequent hydrolysis with aqueous NH4Cl gave the cyclopropanone acetals II (R = Ph, allyl, Me, PhCH2CH2, Et, pentyl; R1 = H) in 66-96% yields. Similar treatment of I with PhMgBr and then with electrophiles, e.g. MeI, trans-cinnamyl chloride, or benzaldehyde, gave disubstituted cyclopropanes, e.g. II [R = Ph; R1 = Me, PhCH(OH), (E)-PhCH:CHCH2]. Enantioselective reaction of I with Et2Zn in toluene containing FeCl3, tetramethylethylenediamine, and (R)-2,2′-bis[bis(4-methylphenyl)phosphino]-1,1′-binaphthyl [(R)-p-tol-BINAP] for 6 days at -10° and one day at 0° followed by hydrolysis with aqueous NH4Cl gave (R)-I (R1 = Et; R2 = H) in 64% yield and 90% ee. In the experiment, the researchers used many compounds, for example, (R)-N,N-Dimethyl-1-[(R)-2-(diphenylphosphino)ferrocenyl]ethylamine (cas: 55700-44-2Reference of 55700-44-2).
(R)-N,N-Dimethyl-1-[(R)-2-(diphenylphosphino)ferrocenyl]ethylamine (cas: 55700-44-2) belongs to chiral phosphine ligands. Generally, the efficiency of nucleophilic phosphine catalysis often depends on the nature of the tertiary phosphine. Chiral phosphine catalysts: Nucleophilic phosphine catalysis often involves the formation of Lewis adducts, namely phosphonium (di)enolate zwitterions, as reaction intermediates.Reference of 55700-44-2
Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis