Redox-Neutral α-C–H Functionalization of Pyrrolidin-3-ol

Yi, Cheng‐Bo; She, Zhi-Ying; Cheng, Yuan; Qu, Jin

doi:10.1021/acs.orglett.7b03807

Cited by 29 publications

(18 citation statements)

References 97 publications

(14 reference statements)

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“…The paramethoxy phenyl group was easily removed by oxidation with CAN which provided a free amine 293 (Scheme 32). [91] Recently, Peddinti et al reported a method of synthesis of C-3 arylation of indoles 296 with para-quinol 294. Iodine was used as a reagent for coupling reactions (Scheme 32).…”

Section: Scheme 29 Reactions Of Para-quinolmentioning

confidence: 99%

“…The para ‐methoxy phenyl group was easily removed by oxidation with CAN which provided a free amine 293 (Scheme 32). [91] …”

Section: Reactions Of Para‐quinols and 25‐cyclo‐hexa‐dienone Monoketalmentioning

confidence: 99%

Section: Application In Natural Product Synthesismentioning

confidence: 99%

“…Oxidative cleavage of 447 and Cbz protection gave the substituted pyrrolidine 448 which was easily converted to natural product by reductive removal of Cbz and nucleophilic cyclization reaction (Scheme 52). [91] Lawrence et al reported the total synthesis of incarviditone and incarvilleatone. Group also revised the structure of incarvilleatone from X-ray analysis of its derivative oxazolidinone.…”

Section: Application In Natural Product Synthesismentioning

confidence: 99%

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Molecular Complexity from Aromatics: Recent Advances in the Chemistry of paraQuinol and Masked para‐Quinone Monoketal

Chandra

Patel

2020

ChemistrySelect

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Synthesis of complex organic molecules from simple, cheap, and readily available starting materials is one of the most challenging and desirable factors in organic synthesis. In the last two decades, various methods have been developed for the de-aromatization reaction of planar aromatics compounds which lead to reactive intermediates like 2,5-cyclohexadienone ketal and para-quinol having a non-planar framework. Recently, there is an upsurge of interest in the development of the chemistry of these intermediates due to their inherent dual electrophilic and nucleophilic character. The presence of diverse functionality makes them important scaffolds and thus these are intensively utilized for the development of methodologies towards the synthesis of the highly functionalized and diverse chemical framework. These synthons have also been used in the total synthesis of many natural products. Interestingly, these are also adaptable for asymmetric synthesis. This review is a summary of the recent development of methods for 2,5-cyclohexadienone ketal and para-quinol synthesis and their application in natural product synthesis.

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Section: Scheme 29 Reactions Of Para-quinolmentioning

confidence: 99%

“…The para ‐methoxy phenyl group was easily removed by oxidation with CAN which provided a free amine 293 (Scheme 32). [91] …”

Section: Reactions Of Para‐quinols and 25‐cyclo‐hexa‐dienone Monoketalmentioning

confidence: 99%

Section: Application In Natural Product Synthesismentioning

confidence: 99%

Section: Application In Natural Product Synthesismentioning

confidence: 99%

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Molecular Complexity from Aromatics: Recent Advances in the Chemistry of paraQuinol and Masked para‐Quinone Monoketal

Chandra

Patel

2020

ChemistrySelect

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“…The resultant carbocation species 139 gave rise to the tetrahydro‐β‐carbolines after aromatization. Following this seminal study, they have reported another imine chemistry, in which fluorinated alcohol stabilized the iminium ion intermediate and expedite nucleophilic addition of the amine to the quinone …”

Section: Miscellaneous Reactionsmentioning

confidence: 99%

Fluorinated Alcohols: Magic Reaction Medium and Promoters for Organic Synthesis

Xiao

2019

The Chemical Record

109

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Fluorinated alcohols have been widely used in the synthetic organic chemistry over the past decades. The unique properties such as the strong hydrogen‐bonding donor ability and low nucleophilicity allow them to promote organic reactions in the absence of any catalyst. These approaches have distinct advantages in terms of operational simplicity, practicability and environmental friendliness. Reactions promoted by fluorinated alcohols, including nucleophilic substitution reactions, annulation reactions, electrophilic reactions, dearomatization reactions, functionalization of multiple bond, epoxidation reactions and miscellaneous reactions have been summarized in this account.

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