161053-46-9Relevant academic research and scientific papers
Axially Chiral Biaryl Monophosphine Oxides Enabled by Palladium/WJ-Phos-Catalyzed Asymmetric Suzuki-Miyaura Cross-coupling
Ji, Wangqin,Wu, Hai-Hong,Zhang, Junliang
, p. 1548 - 1554 (2020/02/04)
A highly enantioselective palladium/WJ-Phos-catalyzed Suzuki-Miyaura coupling reaction for efficient construction of axially chiral biaryl monophosphine oxides was developed. A series of axially chiral biaryl monophosphine oxides were obtained in good yields and with high enantioselectivities. The practicability of this reaction was validated in the straightforward synthesis of axially chiral biaryl monophosphine ligand and demonstrated by a 100-g-scale synthesis. Moreover, various functionalizations of the product make it as a platform molecule for synthesis of other chiral biaryl phosphines.
Stereospecific Functionalization of Axially Chiral 2'-Methoxy-1,1'-binaphthyl-2-carboxylic Acid for the Synthesis of Enantiomerically Pure 2'-Methoxy-1,1'-binaphthyls
Hattori, Tetsutaro,Shijo, Masayuki,Sakamoto, Jun'ichi,Kumagai, Satoshi,Nakajima, Akihiko,Miyano, Sotaro
, p. 124 - 134 (2007/10/02)
Easily accessible, enantiomerically pure (S)-2'-methoxy-1,1'-binaphthyl-2-carboxylic acid (S)-5 is conveniently utilized as the starting material for the preparation of axially chiral 2'-methoxy-1,1'-binaphthyls.The transformations which include Curtius rearrangement of the 2-carboxy group to amine, Sandmeyer iodination, and metalation followed by trapping of the organomagnesium or lithium species with electrophiles proceed with complete retention of the axial chirality of the binaphthyl unit.
Nucleophilic aromatic substitution reactions of 1-methoxy-2- (diphenylphosphinyl)naphthalene with C-, N-, and O-nucleophiles: Facile synthesis of diphenyl(1-substituted-2-naphthyl)phosphines
Hattori,Sakamoto,Hayashizaka,Miyano
, p. 199 - 202 (2007/10/02)
A novel nucleophilic aromatic substitution reaction is described in which the methoxy group of 1-methoxy-2-(diphenylphosphinyl)-naphthalene is readily replaced with Grignard reagents, alkoxides, and amides. Reduction of the resulting phosphine oxides provides a convenient route to diphenyl(1- substituted-2-naphthyl)phosphines.
