Regio- and Stereoselective Cyclization Reactions of Unsaturated Silyl Enol Ethers by Photoinduced Electron Transfer – Mechanistic Aspects and Synthetic Approach

Hintz, Sandra; Mattay, Jochen; Eldik, Rudi van; Fu, Wen‐Fu

doi:10.1002/(sici)1099-0690(199808)1998:8<1583::aid-ejoc1583>3.0.co;2-r

Cited by 37 publications

(17 citation statements)

References 51 publications

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“…. 157 The main adducts of the reaction were cis-1-decalone systems (14.2) in all cases but one in which the alkene was disubstituted at the terminus. In that case, the product was the hexahydroindanone adduct.…”

Section: Oxidative Aryl−aryl Couplingmentioning

confidence: 96%

Organic Photoredox Catalysis

2016

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In this review, we highlight the use of organic photoredox catalysts in a myriad of synthetic transformations with a range of applications. This overview is arranged by catalyst class where the photophysics and electrochemical characteristics of each is discussed to underscore the differences and advantages to each type of single electron redox agent. We highlight both net reductive and oxidative as well as redox neutral transformations that can be accomplished using purely organic photoredox-active catalysts. An overview of the basic photophysics and electron transfer theory is presented in order to provide a comprehensive guide for employing this class of catalysts in photoredox manifolds.

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Section: Oxidative Aryl−aryl Couplingmentioning

confidence: 96%

Organic Photoredox Catalysis

2016

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“…91,92 Silyl enol ethers could also be oxidized and selectively desilylated in the presence of alkyl silyl ethers 93 and Hintz et al later reported a DCA/Phen photocatalytic system for the cyclization of silyl enol ethers with pendant olefins. 94 The Roth laboratory observed altered chemoselectivity in the PET cyclization of geraniol, though the influence of the redox mediator was small. 95 …”

Section: Photoinduced Electron Transfermentioning

confidence: 99%

Dual Catalysis Strategies in Photochemical Synthesis

2016

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The interaction between an electronically excited photocatalyst and an organic molecule can result in the genertion of a diverse array of reactive intermediates that can be manipulated in a variety of ways to result in synthetically useful bond constructions. This Review summarizes dual-catalyst strategies that have been applied to synthetic photochemistry. Mechanistically distinct modes of photocatalysis are discussed, including photoinduced electron transfer, hydrogen atom transfer, and energy transfer. We focus upon the cooperative interactions of photocatalysts with redox mediators, Lewis and Brønsted acids, organocatalysts, enzymes, and transition metal complexes.

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“…8-Hydroxy-3,3a-dihydrocyclopenta [b]chromen-9(2H)-one (15) Prepared from 12 (140 mg, 0.63 mmol) and pyrrolidine (0.02 mL, 0.12 mmol) in toluene (10 mL) by following the general procedure described above yielding 15 (115 mg, 90%) as a yellow viscous mass. IR ν max (film): cm 13 C NMR (50 MHz, CDCl 3 ): δ 180.…”

Section: General Procedures For Bromination Reactionmentioning

confidence: 99%

“…The spectral data matched according to the literature reported data. 15 (3aR*,9aS*)-8-Hydroxy-1,2,3,3a-tetrahydrocyclopenta [b]chromen-9(9aH)-one (28)…”

Section: General Procedures For the Seo 2 Mediated Allylic Oxidationmentioning

confidence: 99%

Antituberculosis agent diaportheone B: synthesis, absolute configuration assignment, and anti-TB activity of its analogues

et al. 2012

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First synthesis of diaportheone B, an antituberculosis agent isolated from endophytic fungus Diaporthe sp. P133 is reported using two complementary routes, a one step and a three-step sequence. The absolute configuration of diaportheone B was determined by using X-ray crystal structure analysis of its dibromo derivative. In addition, we have prepared several close analogues of diaportheone B and determined their anti-TB potential using Alamar-blue assay (H(37)Rv).

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Regio- and Stereoselective Cyclization Reactions of Unsaturated Silyl Enol Ethers by Photoinduced Electron Transfer – Mechanistic Aspects and Synthetic Approach

Cited by 37 publications

References 51 publications

Organic Photoredox Catalysis

Organic Photoredox Catalysis

Dual Catalysis Strategies in Photochemical Synthesis

Antituberculosis agent diaportheone B: synthesis, absolute configuration assignment, and anti-TB activity of its analogues

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