57294-56-1Relevant articles and documents
Synthesis of α,α-Difluorinated Phosphonate pSer/pThr Mimetics via Rhodium-Catalyzed Asymmetric Hydrogenation of β-Difluorophosphonomethyl α-(Acylamino)acrylates
Chen, Hong-Xue,Kang, Jie,Chang, Rong,Zhang, Yun-Lai,Duan, Hua-Zhen,Li, Yan-Mei,Chen, Yong-Xiang
, p. 3278 - 3281 (2018)
A novel and facile synthetic strategy for α,α-difluorinated phosphonate mimetics of phosphoserine/phosphothreonine utilizing rhodium-catalyzed asymmetric hydrogenation was developed. The dehydrogenated substrate β-difluorophosphonomethyl α-(acylamino)acrylates were first prepared from protected serine/threonine followed by asymmetric hydrogenation using the rhodium-DuPhos catalytic system to generate the chiral center(s). These important phosphonate building blocks were successfully incorporated into phosphatase-resistant peptides, which displayed similar inhibition to the 14-3-3 ζ protein as the parent pSer/pThr peptides.
A Five-Step Cascade for the Modular and Regiodefined Synthesis of Naphth[2,1-d]oxazoles
Dinda, Bidyut Kumar,Basak, Shyam,Ghosh, Bidhan,Mal, Dipakranjan
, p. 1235 - 1245 (2016/05/11)
The reaction of 3-nucleofugal phthalides with 2-amidoacrylates is shown to provide a synthesis of densely substituted naphth[2,1-d]oxazoles in good yields. It is proposed to proceed via a five-step cascade which includes phthalide annulation, demethoxycarbonylation, and heterocyclization. The methodology is free from regiochemical ambiguity of the products. In certain cases, the corresponding 2-amidonaphthoquinones are directly formed.
Facile and selective synthesis of chloronicotinaldehydes by the Vilsmeier reaction
Gangadasu,Narender,Bharath Kumar,Ravinder,Ananda Rao,Ramesh,China Raju,Jayathirtha Rao
, p. 8398 - 8403 (2007/10/03)
Eleven enamides were prepared by adopting different procedures. The various enamides prepared were subjected to Vilsmeier reaction using (i) POCl3/DMF; (ii) diphosgene/DMF; (iii) triphosgene/DMF leading to the formation of various multisubstituted chloronicotinaldehydes. Studies carried out indicate that Vilsmeier reagent concentration and the replacement of POCl3 by diphosgene or triphosgene, provides excellent selectivity and higher yields. Under modified reaction conditions one can get only chloronicotinaldehydes and not the chloropyridines as products. The various advantages in using diphosgene and triphosgene are illustrated. The mechanism of formation of chloronicotinaldehyde was discussed.
