Open AccessChiral 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.