Abstract
AbstractWe report a reduction‐condensation‐1,3‐dipolar cycloaddition sequence to create C2‐C3 contiguous stereogenic centers in indoline derivatives. This method includes a one‐pot procedure starting from easily obtainable nitroketones and can be applied to intrarmolecular cycloaddition to give highly functionalized isoxazolidines. Both a length of methylene tether and olefinic substituents strongly affect the cycloaddition mode (exo/endo approach) to give highly stereo‐controlled tri‐ and tetracyclic systems through a single operation. Intermolecular cycloaddition is also applicable to the construction of 3 stereocenters in range of 47–87 % yield.
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