AI Article Synopsis
- The text discusses a new method for an organocatalytic asymmetric [3 + 2] cycloaddition involving β-trifluoromethyl enones and benzothiophene ketimines.
- This reaction produces a variety of spiro pyrrolidine-benzothiophenones with impressive stereocontrol, achieving a ratio of over 20:1 and up to 99% enantiomeric excess.
- The key takeaway is the highly efficient creation of unique spirocyclic compounds, which include a bis(trifluoromethyl)-substituted pyrrolidine structure with four consecutive stereocenters.
Article Abstract
An organocatalytic asymmetric [3 + 2] cycloaddition of β-trifluoromethyl enones with 3-(-2,2,2-trifluoroethyl) benzothiophene ketimines and 2-(-2,2,2-trifluoroethyl) benzothiophene ketimines was described for the first time. A wide spectrum of vicinally bis(trifluoromethyl)-substituted spiro pyrrolidine-benzothiophenones were obtained with excellent stereocontrol (all cases >20:1 dr and up to 99% ee). The highlight of this work is the extremely high efficiency in the construction of spirocyclic benzothiophenone derivatives possessing a vicinally bis(trifluoromethyl)-substituted pyrrolidine moiety with four contiguous stereocenters.
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| http://dx.doi.org/10.1021/acs.orglett.3c03252 | DOI Listing |
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