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Ye, Liu; Tian, Yu; Meng, Xiang; Gu, Qiang‐Shuai; Liu, Xin‐Yuan
Angewandte Chemie International Edition, January 13, 2020, Letnik: 59, Številka: 3Journal Article
Radical‐involved enantioselective oxidative C−H bond functionalization by a hydrogen‐atom transfer (HAT) process has emerged as a promising method for accessing functionally diverse enantioenriched products, while asymmetric C(sp3)−H bond amination remains a formidable challenge. To address this problem, described herein is a dual CuI/chiral phosphoric acid (CPA) catalytic system for radical‐involved enantioselective intramolecular C(sp3)−H amination of not only allylic positions but also benzylic positions with broad substrate scope. The use of 4‐methoxy‐NHPI (NHPI=N‐hydroxyphthalimide) as a stable and chemoselective HAT mediator precursor is crucial for the fulfillment of this transformation. Preliminary mechanistic studies indicate that a crucial allylic or benzylic radical intermediate resulting from a HAT process is involved. Radical control: The first radical‐involved intramolecular enantioselective oxidative C−H amination of not only allylic substrates, but also benzylic substrates, by a hydrogen atom transfer process with a CuI/chiral phosphoric acid catalytic system is reported. Critical to the success is the use of 4‐methoxy‐PINO as a stable and chemoselective hydrogen or.
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Leto | Faktor vpliva | Izdaja | Kategorija | Razvrstitev | ||||
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JCR | SNIP | JCR | SNIP | JCR | SNIP | JCR | SNIP |
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in: SICRIS
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