18295-60-8Relevant articles and documents
Flow Asymmetric Propargylation: Development of Continuous Processes for the Preparation of a Chiral β-Amino Alcohol
Li, Hui,Sheeran, Jillian W.,Clausen, Andrew M.,Fang, Yuan-Qing,Bio, Matthew M.,Bader, Scott
, p. 9425 - 9429 (2017)
The development of a flow chemistry process for asymmetric propargylation using allene gas as a reagent is reported. The connected continuous process of allene dissolution, lithiation, Li-Zn transmetallation, and asymmetric propargylation provides homopropargyl β-amino alcohol 1 with high regio- and diastereoselectivity in high yield. This flow process enables practical use of an unstable allenyllithium intermediate. The process uses the commercially available and recyclable (1S,2R)-N-pyrrolidinyl norephedrine as a ligand to promote the highly diastereoselective (32:1) propargylation. Judicious selection of mixers based on the chemistry requirement and real-time monitoring of the process using process analytical technology (PAT) enabled stable and scalable flow chemistry runs.
Asymmetric Synthesis of Fluorinated Monoterpenic Alkaloid Derivatives from Chiral Fluoroalkyl Aldimines via the Pauson-Khand Reaction
Cabré, Albert,Escorihuela, Jorge,Fustero, Santos,Han, Jianlin,Llobat, Alberto,Mateu, Natalia,Medio-Simón, Mercedes,Riera, Antoni,Román, Raquel,Sedgwick, Daniel M.,Soloshonok, Vadim
supporting information, (2020/02/11)
Enantioenriched fluorinated monoterpenic alkaloid analogues were synthesised, employing a strategy based on the previously undescribed diastereoselective propargylation of fluorinated tert-butanesulfinyl imines, and subsequent Pauson-Khand reaction of res
A novel domino-click approach for the synthesis of sugar based unsymmetrical bis-1,2,3-triazoles
Arora, Bhupinder Singh,Shafi, Syed,Singh, Swarn,Ismail, Tabasum,Kumar, H.M. Sampath
, p. 139 - 144 (2008/09/18)
Aryl or sugar azides were treated with allenylmagnesium bromide to generate 1,5-disubstituted-butynyl-N-aryl or N-glycosyl-1,2,3-bistriazoles in a domino fashion. Upon Cu(I) catalyzed 1,3-dipolar cycloaddition with sugar azides, these compounds afford nov