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Front Cover: Asymmetric Synthesis of 3‐Pyrrolines through an Aryne‐Induced Domino Process (Asian J. Org. Chem. 4/2021)
Author(s) -
Hwu Jih Ru,
Panja Avijit,
Gupta Nitesh K.,
Huang WenChieh,
Hu YuChen,
Lin ChunCheng,
Hwang KuoChu,
Chan WeiJen,
Tsay ShwuChen
Publication year - 2021
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Reports
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.202100140
Subject(s) - chemistry , aryne , domino , cycloaddition , cascade reaction , trimethylsilyl , nucleophile , enantiomer , aryl , combinatorial chemistry , medicinal chemistry , optically active , nucleophilic addition , catalysis , stereochemistry , organic chemistry , alkyl
A new domino reaction is developed for the synthesis of optically active 3‐pyrrolines. The reaction involves the use of (trimethylsilyl)aryl triflates, KF, Schiff bases, and alkynes in the presence of a chiral catalyst (R)‐(–)‐1,1′‐binaphthyl‐2,2′‐diyl hydrogenphosphate. The key features of this reaction include the generation of a single product in very good yields with high stereo‐ and enantioselectivity. The enantiomeric ratio reaches as high as 98.5:1.5. The overall pathway includes four steps in a domino process of 1,2‐elimination, 1,2‐nucleophilic addition, 1,4‐proton shift, and (3+2) cycloaddition. More information can be found in the Full Paper by Jih Ru Hwu et al.