Phosphoric Acid Catalyzed Asymmetric [2+2] Cyclization/Penicillin–Penillonic Acid Rearrangement

Zhang, Ming; Yu, Changjun; Xie, Junqiu; Xun, Xudong; Sun, Wangsheng; Liu, Hong; Wang, Rui

doi:10.1002/anie.201712571

Cited by 32 publications

(4 citation statements)

References 75 publications

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“…Last year, Wang's group reported the first chiral phosphoric acid catalyzed enantioselective [2+2] cycloaddition reactions between azlactones ( 58 ) and N ‐substituted β‐carbolines ( 59 ) (Scheme ) . From the initial generation of an α‐amino‐β‐lactam intermediate ( C ), a sequential phosphoric acid‐catalyzed asymmetric penicillin‐penillonic acid (PPA) rearrangement occurs, leading to the desired imidazoline‐5‐ones ( 60 ) in low to excellent yields (ranging from 36 to 99 %) and excellent enantiomeric excesses (88–99 % ee ).…”

Section: Cycloadditionsmentioning

confidence: 99%

Recent Advances in Azlactone Transformations

2019

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Azlactones, also known as oxazolones, are versatile building blocks in organic synthesis due to the presence of multiple pro‐nucleophilic and electrophilic reactive sites. Recently, several elegant organo‐ and metal‐catalyzed studies have been described, allowing the stereocontrolled access to complex structures in only one or a few chemical steps. Moreover, the development of one‐pot, tandem and domino reactions greatly enhanced the azlactone scaffold potential. In this context, this review aims to cover novel methodologies, including a brief overview of oxazolones and Erlenmeyer azlactones preparation. New approaches towards classical reactions, such as dynamic kinetic resolution, cycloadditions, and conjugate additions will be presented as well as new methodologies involving photochemical and flow chemistry technology. Finally, for most studies, selected examples will be presented and mechanistic pathways and/or activating modes will be carefully discussed.

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Section: Cycloadditionsmentioning

confidence: 99%

Recent Advances in Azlactone Transformations

2019

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“…The penicillin–penillonic acid (PPA) rearrangement, which gives direct access to imidazolidin‐5‐ones, was first reported in 1964 . Very recently, Sun, Hong, Wang and co‐workers described a phosphoric acid catalyzed enantioselective synthesis of imidazolidin‐5‐ones starting from azlactones and N‐substituted dihydrocarbolines. The reaction was proposed to proceed through an initial formal [2+2] cycloaddition leading to the formation of intermediate 109 followed by chiral phosphoric acid catalyzed asymmetric PPA rearrangement via TS‐37 and TS‐38 .…”

Section: Other Enantioselective Rearrangementsmentioning

confidence: 99%

Recent Advances in Catalytic Enantioselective Rearrangement

Wang

Zhu

2019

Eur J Org Chem

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Among the fundamental chemical transformations in organic synthesis, rearrangement has been recognized as powerful and reliable reactions for the construction of carbon–carbon or carbon–heteroatom bonds. Benefiting from the advance of the novel catalytic system, catalyst design and activation mode, the chemistry of enantioselective rearrangements has experienced ever‐growing development recently and has been successfully used in the synthesis of chiral non‐racemic building blocks, natural products, and other valuable compounds. We present herein a survey of the recent development on the catalytic enantioselective rearrangement (from 2013 onward) organized according to the rearrangement type.

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“…5 Its unique 3,9-diazatetracyclo-[6.5.2.0. 1,9 0 3,8 ]pentadec-2-one scaffold attracted organic chemists to undertake the synthesis of its key fragments, [7][8][9][10][11] and its total synthesis. 12,13 Pegaharines C-F represent the first examples of heterodimers featuring a rare tetracyclic β-carboline and a classic tricyclic β-carboline through a C-15-C-1′ bridge, and pegaharine D displayed potent anti-HSV-2 activity.…”

Section: Introductionmentioning

confidence: 99%