4.8 Article

Asymmetric Double Oxidative [3+2] Cycloaddition for the Synthesis of CF3-Containing Spiro[pyrrolidin-3,2?-oxindole]

Journal

ORGANIC LETTERS
Volume 25, Issue 17, Pages 3152-3156

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.3c01083

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An asymmetric double oxidative [3 + 2] cycloaddition is reported, which generates highly functionalized chiral CF3-containing spiro[pyrrolidin-3,2'-oxindole] with four contiguous stereocenters stereoselectively. This method directly constructs two C-C bonds from four C(sp3)-H bonds, and it features mild conditions, broad substrate scope, and excellent functional group compatibility.
An asymmetric double oxidative [3 + 2] cycloaddition is reported. Oxidation of 3-((2,2,2-trifluoroethyl)amino)indolin-2-ones and fi-aryl-substituted aldehydes simultaneously and subsequent asymmetric cycloaddition in the presence of the chiral amino catalyst generated highly functionalized chiral CF3-containing spiro[pyrrolidin-3,2 '-oxindole] with four contiguous stereocenters stereoselectively, which is characterized by directly constructing two C-C bonds from four C(sp3)-H bonds. This new method features mild conditions, broad substrate scope, and excellent functional group compatibility.

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