163926-77-0Relevant academic research and scientific papers
A new method for preparation of 3,6-dihydro-2H-1,3-oxazines and explorations of their use in stereoselective synthesis of 1,3-amino alcohol derivatives
Cherkauskas, John P.,Klos, Andrew M.,Borzilleri, Robert M.,Sisko, Joseph,Weinreb, Steven M.,Parvez, Masood
, p. 3135 - 3152 (1996)
Condensation of β-hydroxy aldehydes with N-sulfonyl aldimines produces 3,6-dihydro-2H-1,3-oxazines in moderate to excellent yields. The process is stereoselective, with the C-2 and C-6 substituents having a trans relationship in these heterocycles. Some transformations of these oxazines as potential acyclic 1,3-amino alcohol synthons are described.
Rhodium-Catalyzed Enantioselective Arylation of Aliphatic Imines
Kato, Naoya,Shirai, Tomohiko,Yamamoto, Yasunori
supporting information, p. 7739 - 7742 (2016/06/09)
Chiral rhodium(I)-catalyzed highly enantioselective arylation of aliphatic N-sulfonyl aldimines with arylboronic acids has been developed. This transformation is achieved by the use of a rhodium/bis(phosphoramidite) catalyst to give enantiomerically enriched α-branched amines (up to 99 % ee). In addition, this system enables efficient synthesis of (+)-NPS R-568 and Cinacalcet which are calcimimetic agents.
Dual gold catalysis: A novel synthesis of bicyclic and tricyclic pyrroles from n -propargyl ynamides
Tokimizu, Yusuke,Wieteck, Marcel,Rudolph, Matthias,Oishi, Shinya,Fujii, Nobutaka,Hashmi, A. Stephen K.,Ohno, Hiroaki
supporting information, p. 604 - 607 (2015/03/05)
Various N-propargyl ynamides were converted to bicylic and tricyclic pyrroles by the use of a cationic dual-activation gold catalyst. This reaction starts with the nucleophilic addition of a gold acetylide onto an ynamide triple bond at the ?2-position of the nitrogen atom. Thus, gold vinylidene is formed, and then a second cyclization takes place. The formation of the gold vinylidene is indicated by the evidence that not only aryl ynamides but also alkyl ynamides undergo C-H activation in these reactions.
Hydrocyanation of sulfonylimines using potassium hexacyanoferrate(II) as an eco-friendly cyanide source
Li, Zheng,Li, Rongzhi,Zheng, Huanhuan,Wen, Fei,Li, Hongbo,Yin, Junjun,Yang, Jingya
, p. 1739 - 1743 (2014/01/06)
An efficient and eco-friendly method for hydrocyanation of sulfonylimines via one-pot two-step procedure using potassium hexacyanoferrate(II) as a cyanide source, benzoyl chloride as a promoter, and potassium carbonate as a base is described. This protocol has the features of using nontoxic, nonvolatile and inexpensive cyanide source, high yield, and simple work-up procedure.
Highly enantioselective arylation of N -tosylalkylaldimines catalyzed by rhodium-diene complexes
Cui, Zhe,Yu, Hong-Jie,Yang, Rui-Feng,Gao, Wen-Yun,Feng, Chen-Guo,Lin, Guo-Qiang
supporting information; experimental part, p. 12394 - 12397 (2011/10/02)
A highly enantioselective rhodium-catalyzed arylation of aliphatic N-tosylaldimines has been developed. The combination of chiral bicyclo[3.3.0]octadiene ligands, an active rhodium hydroxide complex, and neutral reaction conditions is the key to achieving high yield and enantioselectivity. The application of this method is demonstrated by the enantioselective synthesis of chiral 2-aryl pyrrolidines and piperidines in a one-pot procedure. Furthermore, excellent results are also obtained for the imine substrates with the more readily cleavable N-nosyl protecting group.
Preparation of N-p-Tosylaldimines by the Intramolecular Photo-Imino Group Migration of Naphthodithiin-1-N-tosylsulfilimines
Fujii, Takayoshi,Kimura, Takeshi,Furukawa, Naomichi
, p. 1075 - 1078 (2007/10/02)
Naphthodithiin-1-N-tosylsulfilimines (4) were prepared by the reaction of napthodithiins with chloramine-T.Photolysis of 4 undergoes intramolecular imino group rearrangement to give N-tosylaldimines quantitatively together with naphthalene
