Synthesis of chiral non-racemic 2-arylpyrrolines by a [3 + 2] cycloaddition route

Thiagarajan Balasubramanian, Alfred Hassner

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A new and efficient diastereoselective (upto 76% de) synthesis of 2-aryl-3-pyrroline derivatives 3a-f has been achieved by [3 + 2] cycloaddition of allylsulfone 1 and non-racemic sulfinimines 2. Separation of the diastereomers led to optically pure 2(R)-pyrrolines (62-72% yield). The N-sulfinyl auxiliary can be removed with TFA.

Original languageEnglish
Pages (from-to)5755-5758
Number of pages4
JournalTetrahedron Letters
Issue number32
StatePublished - 5 Aug 1996

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Scheme 2 In summary, this methodology based on Michael addition of I to (S)-sulfinimines 2 serves as a novel and efficient stereoselective route to optically active 2(R)-arylpyrroline derivatives. Starting from (R)(-) sulfinimines 2 and 1, the antipode of 3 can be prepared. Further elaboration of these chiral pyrrolines is in progress. Acknowledgement: We are grateful to the US-Israel Binational Science Foundation and the Israel Science Foundation for support of this research. We thank Dr.H.E.Gottlieb for help with the NMR spectra, Dr.M. Cojocaru for help with the mass spectra, and Professor E.Ghera for helpful discussions.


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