Electroorganic chemistry. 31. Reductive cyclization of nonconjugated olefinic ketones to cyclic tertiary alcohols

Shono, Tatsuya; Nishiguchi, Ikuzo; Ohmizu, Hiroshi; Mitani, Makoto

doi:10.1021/ja00470a031

Cited by 119 publications

(32 citation statements)

References 9 publications

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“…The intramolecular cathodic cross coupling between a carbonyl group and a double bond produces cyclopentanes in high diastereoselectivity; in this cyclization possibly radicals or anion radicals are involved (Scheme 30) [58].…”

Section: Carbonyl Compoundsmentioning

confidence: 99%

Contributions of organic electrosynthesis to green chemistry

Schäfer

2011

Comptes Rendus. Chimie

254

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Section: Carbonyl Compoundsmentioning

confidence: 99%

Contributions of organic electrosynthesis to green chemistry

Schäfer

2011

Comptes Rendus. Chimie

254

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“…24,40 A similar procedure for the generation of ketyl radicals by using SmI 2 /DMPU in at least stoichiometric amounts has been reported by Motherwell. 41 Contrary to these methods and to electroreduction, 42 the photochemical approach is of high preparative value due to its simple procedure. In addition, heterogeneous conditions as used in the reaction with Zn/Me 3 SiCl 40 and SmI 2 /DMPU 41 sometimes cause difficulties.…”

Section: Biographical Sketchesmentioning

confidence: 99%

Rearrangement and Cyclization Reactions by Photoinduced Electron Transfer: New Approaches for the Synthesis of Polycyclic Compounds

Waske¹,

Tzvetkov²,

Mattay³

2007

Synlett

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The concept of intramolecular radical ion cyclization reactions by photoinduced electron transfer (PET) is a powerful tool for constructing complex carbocyclic and heterocyclic ring systems. In this account we describe our earlier investigations in this field followed by the development of new approaches to the synthesis of polycyclic compounds. Radical ions generated by single-electron transfer (SET) from suitable neutral molecules are used as decisive intermediates in a wide range of interesting cyclization processes and reactions. Various synthetic strategies are presented involving radical anionic or radical cationic species generated by reductive and oxidative PET, respectively. 1 Introduction 2 General Concept 3 Reductive Electron Transfer: Formation of Ketyl and g-Keto Radicals 4 Oxidative Electron Transfer: Formation of a-and b-Keto Radicals 5 Su mmary

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“…As shown earlier by Shono et al &e-and e,(-unsaturated ketones similar to 172 also cyclize under electroreductive conditions with remarkable regio-and stereoselectivity. In a mixed solvent of methanol and dioxane or in N,N-dimethylformamide using carbon electrodes, cis isomers of exocyctic tertiary alcohols 174 are exclusively obtained in yields of 32 to 87% [176,177]. Due to the stereoselectivty and the mild conditions, the PETreductive cyclization reaction has been applied to the total synthesis of polycyclic and heterocyclic biologically active natural products such as ( + ) Hirsutene 180 [178,179] or ( _ ) Isooxyskyanthine 183 [180].…”

Section: Isooxyskytanthinementioning

confidence: 99%