187679-57-8Relevant articles and documents
Synthesis of 2-Arylpiperidines via pd-catalyzed arylation of aza-Achmatowicz rearrangement products with arylboronic acids
Zhao, Guodong,Canterbury, Daniel P.,Taylor, Alexandria P.,Cheng, Xiayun,Mikochik, Peter,Bagley, Scott W.,Tong, Rongbiao
, p. 458 - 463 (2020/01/21)
The first Pd-catalyzed arylation of aza-Achmatowicz rearrangement products with arylboronic acids is achieved, providing versatile 2-Aryldihydropyridinones for facile synthesis of highly functionalized 2-Arylpiperidines. Key to this arylation is the use of non-phosphine-ligand palladium precatalyst. The substrate scope is demonstrated with >26 examples, and the utility of 2-Aryldihydropyridinones is illustrated by the synthesis of a small collection of 2-Arylpiperidines with substituents or functional groups at any carbon (C2-C6) as well as two NK1 receptor antagonists (+)-CP-999,94 and (+)-L-733,060.
Concise asymmetric synthesis of (+)-CP-99,994 and (+)-l-733,060 via efficient construction of homochiral syn-1,2-diamines and syn-1,2-amino alcohols
Liu, Run-Hua,Fang, Kai,Wang, Bing,Xu, Ming-Hua,Lin, Guo-Qiang
, p. 3307 - 3310 (2008/09/20)
(Chemical Equation Presented) An efficient asymmetric synthesis of human NK-1 SP receptor antagonists (+)-CP-99,994 and (+)-L-733,060 was achieved starting from a common chiral intermediate (5). Our route featured the SmI 2-induced reductive co
Enantioselective synthesis of primary 1-(aryl)alkylamines by nucleophilic 1,2-addition of organolithium reagents to hydroxyoxime ethers and application to asymmetric synthesis of G-protein-coupled receptor ligands
Atobe, Masakazu,Yamazaki, Naoki,Kibayashi, Chihiro
, p. 5595 - 5607 (2007/10/03)
(E)-Arylaldehyde oxime ethers bearing a (1S)-2-hydroxy-1-phenylethyl or (2R)-1-hydroxy-2-phenylethyl group as a chiral auxiliary, both derived from a single precursor, methyl (R)-mandelate, underwent nucleophilic addition with organolithium reagents via six-membered chelates to give the diastereomerically enriched (R)- and (S)-adducts, respectively, which, after chiral auxiliary removal by reductive N-O bond cleavage, led to the corresponding (R)- and (S)-1-(aryl)ethylamines. This organolithium addition protocol using methyllithium was applied in an enantiodivergent fashion to the preparation of both enantiomers of 1-(2-hydroxyphenyl)ethylamine, which has been previously used as an efficient chiral auxiliary for the synthesis of natural products in this laboratory. The synthetic utility of this methodology involving diastereoselective methyl addition was demonstrated by further application to the asymmetric synthesis of a new type of calcium receptor agonist (calcimimetics), (R)-(+)-NPS R-568 and its thio analogue. Furthermore, diastereoselective vinylation was accomplished by application of the hydroxy oxime ether-based protocol using vinyllithium, which allowed the development of the enantioselective synthesis of the NK-1 receptor antagonists, (+)-CP-99,994 and (+)-CP-122,721.
