Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 58, Issue 46, Pages 16637-16643Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201908227
Keywords
azomethine ylides; copper; cycloaddition; fluorine; synthetic methods
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Funding
- National Natural Science Foundation of China [21573169, 21772151]
- Natural Science Foundation of Hubei Province [2018CFA084]
- Wuhan Morning Light Plan of Youth Science and Technology [2017050304010314]
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A Cu-II-catalyzed asymmetric 1,3-dipolar cycloaddition using beta-fluoroalkyl alkenyl arylsulfones as dipolarophiles and glycine/alanine iminoesters as azomethine ylide precursors has been developed. Remarkably, a catalyst loading as low as 0.5 mol % is highly efficient. Accordingly, a wide range of enantioenriched 3-fluoroalkyl pyrrolidines, as well as Delta(2)-pyrroline and pyrrole derivatives, are generated in good to excellent yields with high asymmetric induction. This synthetic approach is diastereodivergent in that exo-adducts could be converted into the corresponding exo '-adducts by 1,8-diazabicyclo[5.4.0]undec-7-ene mediated epimerization at C2 of the pyrrolidine core. The free-energy profiles from DFT calculations suggest the Michael addition of the 1,3-dipole to be the rate- and enantiodetermining step, and the origin of stereoselectivity is studied by means of the noncovalent interaction (NCI) analysis.
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