Abstract
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 language | English |
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Pages (from-to) | 5755-5758 |
Number of pages | 4 |
Journal | Tetrahedron Letters |
Volume | 37 |
Issue number | 32 |
DOIs | |
State | Published - 5 Aug 1996 |
Bibliographical note
Funding Information: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.
Funding
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.
Funders | Funder number |
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United States-Israel Binational Science Foundation | |
Israel Science Foundation |