944814-28-2Relevant academic research and scientific papers
Nickel-Catalyzed Enantioselective Reductive Cross-Coupling of Styrenyl Aziridines
Woods, Brian P.,Orlandi, Manuel,Huang, Chung-Yang,Sigman, Matthew S.,Doyle, Abigail G.
, p. 5688 - 5691 (2017)
A Ni-catalyzed reductive cross-coupling of styrenyl aziridines with aryl iodides is reported. This reaction proceeds by a stereoconvergent mechanism and is thus amenable to asymmetric catalysis using a chiral bioxazoline ligand for Ni. The process allows
Asymmetric [3+2] Annulation Approach to 3-Pyrrolines: Concise Total Syntheses of (-)-Supinidine, (-)-Isoretronecanol, and (+)-Elacomine
Chogii, Isaac,Njardarson, Jon T.
supporting information, p. 13706 - 13710 (2015/11/16)
An asymmetric [3+2] annulation reaction to form 3-pyrroline products is reported. Upon treatment with lithium diisopropylamide, readily available ethyl 4-bromocrotonate is deprotonated and trapped with Ellman imines selectively at the α-position to yield enantiopure 3-pyrroline products. This new method is compatible with aryl, alkyl, and vinyl imines. The efficacy of the method is showcased by short asymmetric total syntheses of (-)-supinidine, (-)-isoretronecanol, and (+)-elacomine. This novel annulation approach also works for an aldehyde, thus providing access to a 2,5-dihydrofuran product in a single step from simple precursors. By modifying the structure of the carbanion nucleophile, an asymmetric vinylogous aza-Darzens reaction can be realized.
Enantioselective synthesis of H -phosphinic acids bearing natural amino acid residues
Yao, Qiuli,Yuan, Chengye
supporting information, p. 6962 - 6974 (2013/08/23)
The first systematic study on the asymmetric synthesis of H-phosphinic acids bearing natural protein amino acid residues was reported on the basis of the asymmetric addition of ethyl diethoxymethylphosphinate to N-tert-butanesulfinyl imines. Good yields a
