Journal
ORGANIC LETTERS
Volume 25, Issue 42, Pages 7667-7672Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.3c02969
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A chiral sulfoximine-enabled Ru-(II)-catalyzed asymmetric C-H activation/functionalization process has been developed for the synthesis of dihydrobenzofuran- or indoline-fused isoquinolinones with a tertiary or quaternary stereocenter. The method achieves high yields and enantioselectivities (up to 97:3 enantiomeric ratio) and allows for the recovery and reuse of the chiral sulfoxide precursor.
Developed herein is a chiral sulfoximine-enabled Ru-(II)-catalyzed asymmetric C-H activation/functionalization involving intramolecular hydroarylation and functionalization/annulation of alkynes. This process constructs dihydrobenzofuran- or indoline-fused isoquinolinones having a tertiary or quaternary stereocenter with good yields and enantioselectivities (up to 97:3 enantiomeric ratio). The chiral sulfoxide precursor used in synthesizing the enantiopure sulfoximines is spontaneously eliminated during the reaction. It can be recovered without losing enantiopurity (similar to 99% enantiomeric excess) and reused.
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