Chiral Bifunctional Phosphine Ligand Enables Gold-Catalyzed Asymmetric Isomerization and Cyclization of Propargyl Sulfonamide into Chiral 3-Pyrroline | Zendy

Xinpeng Cheng | Zendy; Liming Zhang | Zendy

Open Access

Chiral Bifunctional Phosphine Ligand Enables Gold-Catalyzed Asymmetric Isomerization and Cyclization of Propargyl Sulfonamide into Chiral 3-Pyrroline

Author(s) -

Xinpeng Cheng,

Liming Zhang

Publication year - 2021

Publication title -

organic letters

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.94

H-Index - 239

eISSN - 1523-7060

pISSN - 1523-7052

DOI - 10.1021/acs.orglett.1c02896

Subject(s) - chemistry , phosphine , propargyl , isomerization , pyrroline , bifunctional , ligand (biochemistry) , catalysis , sulfonamide , combinatorial chemistry , organic chemistry , medicinal chemistry , receptor , biochemistry

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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