Chiral Bifunctional Phosphine Ligand Enables Gold-Catalyzed Asymmetric Isomerization and Cyclization of Propargyl Sulfonamide into Chiral 3‑Pyrroline
This work details an asymmetric gold-ligand cooperative catalysis that transforms readily accessible chiral/achiral propargylic sulfonamides into chiral 3-pyrrolines. A bifunctional biphenyl-2-ylphosphine ligand featuring a chiral tetrahydroisoquinoline fragment is essential for the observed metal–l...
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| Published in | Organic letters Vol. 23; no. 21; pp. 8194 - 8198 |
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| Main Authors | , |
| Format | Journal Article |
| Language | English |
| Published |
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American Chemical Society
05.11.2021
Amer Chemical Soc |
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| Abstract | This work details an asymmetric gold-ligand cooperative catalysis that transforms readily accessible chiral/achiral propargylic sulfonamides into chiral 3-pyrrolines. A bifunctional biphenyl-2-ylphosphine ligand featuring a chiral tetrahydroisoquinoline fragment is essential for the observed metal–ligand cooperation and the asymmetric induction. 2,5-cis-3-Pyrrolines are formed with excellent diastereoselectivities in a “matched” scenario. The “mismatched” scenario by using the ligand enantiomer delivers 2,5-trans-3-pyrrolines with >5/1 diastereoselectivity. The synthetic utilities of this chemistry are demonstrated. |
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| AbstractList | This work details an asymmetric gold-ligand cooperative catalysis that transforms readily accessible chiral/achiral propargylic sulfonamides into chiral 3-pyrrolines. A bifunctional biphenyl-2-ylphosphine ligand featuring a chiral tetrahy-droisoquinoline fragment is essential for the observed metal-ligand cooperation and the asymmetric induction. 2,5-cis-3-Pyrrolines are formed with excellent diastereoselectivities in a "matched" scenario. The "mismatched" scenario by using the ligand enantiomer delivers 2,5-trans-3-pyrrolines with >5/1 diastereoselectivity. The synthetic utilities of this chemistry are demonstrated. This work details an asymmetric gold-ligand cooperative catalysis that transforms readily accessible chiral/achiral propargylic sulfonamides into chiral 3-pyrrolines. A bifunctional biphenyl-2-ylphosphine ligand featuring a chiral tetrahydroisoquinoline fragment is essential for the observed metal–ligand cooperation and the asymmetric induction. 2,5-cis-3-Pyrrolines are formed with excellent diastereoselectivities in a “matched” scenario. The “mismatched” scenario by using the ligand enantiomer delivers 2,5-trans-3-pyrrolines with >5/1 diastereoselectivity. The synthetic utilities of this chemistry are demonstrated. This work details an asymmetric gold-ligand cooperative catalysis that transforms readily accessible chiral/achiral propargylic sulfonamides into chiral 3-pyrrolines. A bifunctional biphenyl-2-ylphosphine ligand featuring a chiral tetrahydroisoquinoline fragment is essential for the observed metal−ligand cooperation and the asymmetric induction. 2,5- cis -3-Pyrrolines are formed with excellent diastereoselectivities in a “matched” scenario. The “mismatched” scenario by using the ligand enantiomer delivers 2,5- trans -3-pyrrolines with >5/1 diastereoselectivity. The synthetic utilities of this chemistry are demonstrated. |
| Author | Cheng, Xinpeng Zhang, Liming |
| AuthorAffiliation | Department of Chemistry and Biochemistry |
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| Author_xml | – sequence: 1 givenname: Xinpeng surname: Cheng fullname: Cheng, Xinpeng – sequence: 2 givenname: Liming orcidid: 0000-0002-5306-1515 surname: Zhang fullname: Zhang, Liming email: zhang@chem.ucsb.edu |
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| Title | Chiral Bifunctional Phosphine Ligand Enables Gold-Catalyzed Asymmetric Isomerization and Cyclization of Propargyl Sulfonamide into Chiral 3‑Pyrroline |
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