An Epoxidation Approach to a Chiral Lactone:  Application of the Shi Epoxidation

Ager, David J.; Anderson, Ken B.; Oblinger, Eric; Shi, Yian; Vanderroest, J. M.

doi:10.1021/op060140e

Cited by 50 publications

(21 citation statements)

References 19 publications

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“…The Suzuki reaction is an arguably efficient method for aryl–aryl bond formation since initial reports in 1979 . The development of the Suzuki reaction has proceeded, including boronic acid and aryl chloride coupling, boronic acid and aryl bromide coupling, boronic acid and aryl iodide coupling, boronic acid and alkenyl triflate coupling, borane and aryl halide coupling, borane and alkyl halide coupling, boronic ester and aryl halide coupling, boronic ester and alkyl halide coupling, borate complexes, etc.…”

Section: Preparation Routes To Cmpsmentioning

confidence: 99%

Design, preparation and application of conjugated microporous polymers

et al. 2013

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Conjugated microporous polymers (CMPs) are of great interest because these types of materials have high specific surface area and pore diameters less than 2 nm. CMPs have found applications in the fields of hydrogen storage, heterogeneous catalysts, gas-permeable membranes and light-emitting organics. A large number of recent reports have demonstrated that CMPs can be prepared using several approaches like noble metal-mediated ethynyl, Sonogashira-Hagihara coupling, Suzuki coupling and Yamamoto coupling reactions. In this review, the synthetic routes, functionalization and potential applications of CMPs are systematically introduced.

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Section: Preparation Routes To Cmpsmentioning

confidence: 99%

Design, preparation and application of conjugated microporous polymers

et al. 2013

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“…[61] On a pilot-plant scale, the di-A C H T U N G T R E N N U N G siamylborane 47 was reacted with 3-fluorobenzyl chloride (48) to give 49 using the standard precatalyst PdA C H T U N G T R E N N U N G (OAc) 2 /PPh 3 (Scheme 15). The versatility of this reaction also allows the linkage of a CA C H T U N G T R E N N U N G (sp 2 ) center and a CA C H T U N G T R E N N U N G (sp 3 ) center, even on an industrial scale.…”

Section: Suzuki-miyaura Reactionsmentioning

confidence: 99%

“…Ager and co-workers at DSM identified and developed an elegant method to produce large amounts of lactone 46, a precursor to potential HIV drugs and blood pressure modulation agents. [61] On a pilot-plant scale, the di-A C H T U N G T R E N N U N G siamylborane 47 was reacted with 3-fluorobenzyl chloride (48) to give 49 using the standard precatalyst PdA C H T U N G T R E N N U N G (OAc) 2 /PPh 3 (Scheme 15). Then, the Suzuki coupling product 49 was transformed into 46 via organocatalytic Shi epoxidation.…”

Section: Suzuki-miyaura Reactionsmentioning

confidence: 99%

Recent Applications of Palladium‐Catalyzed Coupling Reactions in the Pharmaceutical, Agrochemical, and Fine Chemical Industries

2009

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Palladium-catalyzed coupling reactions have become a central tool for the synthesis of biologically active compounds both in academia and industry. Most of these transformations make use of easily available substrates and allow for a shorter and more selective preparation of substituted arenes and heteroarenes compared to non-catalytic pathways. Notably, molecular-defined palladium catalysts offer high chemoselectivity and broad functional group tolerance. Considering these advantages, it is not surprising that several palladium-catalyzed coupling reactions have been implemented in the last decade into the industrial manufacture of pharmaceuticals and fine chemicals. In this review different examples from 2001-2008 are highlighted, which have been performed at least on a kilogram scale in the chemical and pharmaceutical industries.

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“…Crude alkene 127, prepared from 4-pentynoic acid by hydroboration and Suzuki coupling with 3-fluorobenzyl chloride, was epoxidized with ketone 42 to give lactone 128 (59 lb) in around 63% overall yield and 88% ee after cyclization, without need for isolation of any intermediates during the entire process (Scheme 3.41) [81].…”

Section: ) [24f ] Such Interactions Are Also Supported Bymentioning

confidence: 99%

Organocatalytic Oxidation. Ketone‐Catalyzed Asymmetric Epoxidation of Alkenes and Synthetic Applications

Shi

2010

Modern Oxidation Methods

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The asymmetric epoxidation of alkenes constitutes a powerful approach to enantiomerically enriched epoxides, a class of highly versatile intermediates in organic synthesis [1]. Various effective epoxidation systems have been developed, including epoxidation of allylic [2, 3] and homoallylic [4] alcohols, metal-catalyzed epoxidation of unfunctionalized alkenes [5][6][7], and the nucleophilic epoxidation of electron-deficient alkenes [8]. During the past 10-15 years, much effort has been devoted to chiral ketone-catalyzed asymmetric epoxidation (Scheme 3.1). The subject has been described in great detail in the first edition [9] and other reviews [10]. This chapter provides an update on progress in this area since the first edition [9].Scheme 3.1 Chiral ketone-catalyzed asymmetric epoxidation of alkenes.Modern Oxidation Methods. Edited by Jan-Erling Bäckvall

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An Epoxidation Approach to a Chiral Lactone: Application of the Shi Epoxidation

Cited by 50 publications

References 19 publications

Design, preparation and application of conjugated microporous polymers

Design, preparation and application of conjugated microporous polymers

Recent Applications of Palladium‐Catalyzed Coupling Reactions in the Pharmaceutical, Agrochemical, and Fine Chemical Industries

Organocatalytic Oxidation. Ketone‐Catalyzed Asymmetric Epoxidation of Alkenes and Synthetic Applications

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