1309980-37-7Relevant articles and documents
Synthesis of 2-aziridinyl phosphonates by modified Gabriel-Cromwell reaction and their antibacterial activities
Do?an, ?zdemir,Babiz, Hakan,G?zen, Ay?e Gül,Budak, Songül
, p. 2485 - 2489 (2011)
A set of new aziridinyl phosphonates (4a-g) were synthesized by using the Gabriel-Cromwell reaction and its modified version developed in this study and their structures confirmed by HRMS, IR, and NMR spectra. All the compounds were screened for their antibacterial activity. They all showed comparable moderate to good growth inhibitory activity in reference to ampicillin and streptomycin.
α-Phosphonovinyl Arylsulfonates: An Attractive Partner for the Synthesis of α-Substituted Vinylphosphonates through Palladium-Catalyzed Suzuki Reactions
Fang, Yewen,Zhang, Li,Jin, Xiaoping,Li, Jinjian,Yuan, Meijuan,Li, Ruifeng,Wang, Tong,Wang, Tao,Hu, Hanjun,Gu, Juejun
, p. 1577 - 1587 (2016/04/05)
It has been demonstrated that a variety of α-phosphonovinyl arylsulfonates with electron-neutral, -donating, and -withdrawing groups on the phenyl ring could be conveniently and efficiently prepared. In the presence of a Pd(OAc)2/SPhos-based catalyst, various organoboron compounds could be employed as the nucleophilic coupling partners, such as organoboronic acids, boronate esters, and organotrifluoroborates. The newly developed O-centered electrophiles could couple with a multitude of aryl, heteroaryl, and alkylboron reagents, to give α-substituted vinylphosphonates in moderate to excellent yields. Generally, the Suzuki reaction is tolerant of extensive substitution at the aromatic ring of both electrophilic and nucleophilic coupling partners. As in the case of the Suzuki reaction of 8-quinolineboronic acid, proper choice of α-phosphonovinyl arylsulfonates is critical to efficient coupling. Moreover, the prospect for application of this method to complex synthesis has been demonstrated through the coupling of estrone-derived arylborons. The present protocol also features mild conditions and high efficiency. A new and attractive coupling partner for the synthesis of α-substituted vinylphosphonates through Suzuki reactions has been developed. The developed O-centered electrophiles couple with various organoboron reagents to give α-substituted vinylphosphonates in moderate to excellent yields. This protocol features broad substrate scope, mild conditions, and high efficiency.
New phosphine oxide aziridinyl phosphonates as chiral Lewis bases for the Abramov-type phosphonylation of aldehydes
Dogan, Oezdemir,Isci, Muhammet,Aygun, Muhittin
, p. 562 - 567 (2013/06/27)
A series of Lewis bases were screened for Abramov-type phosphine additions to aldehydes. A novel phosphine oxide aziridinyl phosphonate POAP-A was found to be better than the others in forming the product in 96% yield and with 42% ee. The absolute configu
