- Site- And enantiodifferentiating C(sp3)-H oxidation enables asymmetric access to structurally and stereochemically diverse saturated cyclic ethers
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A manganese-catalyzed site- and enantiodifferentiating oxidation of C(sp3)-H bonds in saturated cyclic ethers has been described. The mild and practical method is applicable to a range of tetrahydrofurans, tetrahydropyrans, and medium-sized cyclic ethers with multiple stereocenters and diverse substituent patterns in high efficiency with extremely efficient site- and enantiodiscrimination. Late-stage application in complex biological active molecules was further demonstrated. Mechanistic studies by combined experiments and computations elucidated the reaction mechanism and origins of stereoselectivity. The ability to employ ether substrates as the limiting reagent, together with a broad substrate scope, and a high level of chiral recognition, represent a valuable demonstration of the utility of asymmetric C(sp3)-H oxidation in complex molecule synthesis.
- Liu, Lei,Sun, Shutao,Yang, Yiying,Zhang, Dongju,Zhao, Ran
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supporting information
p. 19346 - 19353
(2020/12/01)
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- Synthesis of α-Cyano and α-Sulfonyl Cyclic Ethers via Intramolecular Reactions of Peroxides with Sulfone- And Nitrile-Stabilized Carbanions
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The intramolecular reaction of carbon nucleophiles with oxygen-centered electrophiles has been little explored outside of nucleophilic epoxidation. We now report the synthesis of sulfonyl- and cyano-substituted oxacycles via intramolecular reaction of sul
- Horn, Alissa,Dussault, Patrick H.
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p. 14611 - 14626
(2019/11/13)
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- Direct radical sulfonylation at α-C(sp3)-H of THF with sodium sulfinates in aqueous medium
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A direct transition-metal-free, convenient and highly regioselective synthesis of 2-alkyl/aryl sulfonyl tetrahydrofurans (THFs) has been achieved from THF and sodium sulfinates using K2S2O8 as a mild oxidant. This one-pot
- Singh, Manjula,Yadav, Lal Dhar S.,Singh, Rana Krishna Pal
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supporting information
p. 810 - 813
(2019/02/20)
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- PREPARATION AND REACTIONS OF 2-BENZENESULPHONYLTETRAHYDROPYRAN
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The anion derived from 2-benzenesulphonyltetrahydropyran (1) reacts with various electrophiles to give alkylated or acylated products some of which are useful precursors for spiroketal synthesis.
- Ley, Steven V.,Lygo, Barry,Wonnacott, Anne
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p. 535 - 538
(2007/10/02)
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