Data from: Organocatalytic enantioselective addition of 3-aryloxindoles to ethenesulfonyl fluoride
Abstract
We report the synthesis of chiral sulfonyl fluorides bearing a carbon quaternary stereocenter. A commercially available organocatalyst (DHQD)2AQN enables the enantioselective addition of 3-substituted oxindoles to ethenesulfonyl fluoride (ESF), achieving excellent yields (27-99%) and enantioselectivities (89-99% ee) for 3-arylsubstituted oxindoles. This methodology shows high functional group tolerance, as demonstrated by successfully engaging halides, ethers, nitriles, acetals, ketals, or heteroaromatic substituents. The utility of the described products was proven by various synthetic transformations, including SuFEx reactions with complex biomolecules.
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2a 95%, 97% ee 99%, 98% ee 2h 91%, 98% ee 2l 83%, 89% ee 2r 80%, 72% ee N O S O F O Boc 2b 41%, 31% ee N O S O F O Ac 2c 33%, 19% ee N O S O F O Bn 2d 96%, 98% ee N O S O F O Boc 2o 89%, 96% ee N O S O F O Boc 2u 89%, 7:1 dr 90% ee: 79% ee N O S O F O Boc Me F 2j 79%, 97% ee N O S O F O Boc 2n 85%, 98% ee N O S O F O Boc 2t 88% 98% ee F OMe N O S O F O Boc N O S O F O Boc N O S O F O Boc MeO Me H O 2e 92%, 97% ee N O S O F O Boc Cl 2i 90%, 95% ee N O S O F O Boc 2s 74%, 97% ee N O S O F O Boc 2g 99%, 98% ee N O S O F O Boc 2m 99%, 96% ee N O S O F O Boc Cl MeO Cl 2f 89%, 98% ee N O S O F O Boc Br 2p 99%, 90% ee N O S O F O Boc N 2k 27%, 90% ee N O S O F O Boc Me Me 2q 65%, 70% ee N O S O F O Boc CO 2 Me 2w 88%, 53% ee N O Me S O F O Boc 2x 71%, 30% ee N O S O F O Boc 2v 92%, 99% ee N O S O F O Boc N Me O OH N O S O F O Boc O OCF3 4 85%, 98%ee 3 93%, 98%ee N O Ph S O O O Boc O O N H O Ph S O N O O CH3O H H H O 6 76%, dr > 20:1 5 96%, dr > 20:1 NO Ph S OO Boc N O Boc SO O O O O O OO 7 (95% ee) N O Ph S O F O Boc N O Boc SO2F 2z 6% N O Boc SO2F 2y 16%, 23%ee N O Boc SO2F FO2S 17