Enantioselective access to multi-cyclic α-amino phosphonates <i>via</i> carbene-catalyzed cycloaddition reactions between enals and six-membered cyclic imines

Sun, Jun; Mou, Chengli; Liu, Changyi; Huang, Ruoyan; Zhang, Shupeng; Zheng, Pengcheng; Robin, Yonggui

doi:10.1039/c8qo00877a

Cited by 30 publications

(12 citation statements)

References 71 publications

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“… Sun et al (2018 ) reported the synthesis of novel aminophosphonates via the aza-formal [4 + 2] cycloaddition reaction between the β -methyl- α , β -unsaturated aldehyde and the cyclic ketiminophosphonate in the presence of 5 mol% of NHC (N-heterocyclic carbene) as the chiral catalyst and 120 mol% of dibenzoquinone as the external oxidant. The antibacterial properties of synthesized products were assayed against X. oryzae pv.…”

Section: Biological Activation Of Hydroxy- and Amino-phosphonates And...mentioning

confidence: 99%

Hydroxy- and Amino-Phosphonates and -Bisphosphonates: Synthetic Methods and Their Biological Applications

et al. 2022

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Phosphonates and bisphosphonates are stable analogs of phosphates and pyrophosphates that are characterized by one and two carbon–phosphorus bonds, respectively. Among the various phosphonates and bisphosphonates, hydroxy and amino substitutes are of interest as effective in medicinal and industrial chemistry. For example, hydroxy bisphosphonates have proven to be effective for the prevention of bone loss, especially in osteoporotic disease. On the other hand, different substitutions on the carbon atom connected to phosphorus have led to the synthesis of many different hydroxy- and amino-phosphonates and -bisphosphonates, each with its distinct physical, chemical, biological, therapeutic, and toxicological characteristics. Dialkyl or aryl esters of phosphonate and bisphosphonate compounds undergo the hydrolysis process readily and gave valuable materials with wide applications in pharmaceutical and agriculture. This review aims to demonstrate the ongoing preparation of various classes of hydroxy- and amino-phosphonates and -bisphosphonates. Furthermore, the current review summarizes and comprehensively describes articles on the biological applications of hydroxyl- and amino-phosphonates and -bisphosphonates from 2015 until today.

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Section: Biological Activation Of Hydroxy- and Amino-phosphonates And...mentioning

confidence: 99%

Hydroxy- and Amino-Phosphonates and -Bisphosphonates: Synthetic Methods and Their Biological Applications

et al. 2022

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“…Moreover, although not strictly a cycloaddition reaction, in 2018, Chi’s group reported the use of five- and six-membered cyclic α-iminophosphonates 229 in a N -heterocyclic carbene XXV -catalyzed formal [4+2] cycloaddition with α,β-unsaturated aldehydes 230 ( Scheme 46 ) [ 86 , 87 ].…”

Section: Enantioselective Synthesis Of Tetrasubstituted α-Aminophosphonic Acid Derivativesmentioning

confidence: 99%

Asymmetric Synthesis of Tetrasubstituted α-Aminophosphonic Acid Derivatives

et al. 2021

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Due to their structural similarity with natural α-amino acids, α-aminophosphonic acid derivatives are known biologically active molecules. In view of the relevance of tetrasubstituted carbons in nature and medicine and the strong dependence of the biological activity of chiral molecules into their absolute configuration, the synthesis of α-aminophosphonates bearing tetrasubstituted carbons in an asymmetric fashion has grown in interest in the past few decades. In the following lines, the existing literatures for the synthesis of optically active tetrasubstituted α-aminophosphonates are summarized, comprising diastereoselective and enantioselective approaches.

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Section: Figurementioning

confidence: 99%

“…The same research group have extended the scope of the reaction with cyclic ketiminophosphonates 92 as the coupling partners to enals 89 instead of cyclic sulfonyl imines to construct α-amino phosphonates 93 with extraordinarily high ee values (Scheme 25). [51] The formation of vinyl enolate intermediate 94 from enal and the carbene is the important step of this enantioselective aza-[4 + 2] cycloaddition followed by the successive addition of ketiminophosphonates 92 to generate 95 which releases free carbene along with the desired α-amino phosphonates 93 in good yields and excellent enatioselectivities. The chemical utility of the present strategy was that this [4 + 2] cycloaddition could be applied for the gram-scale synthesis with the expected α-amino phosphonates in good yields and excellent eantioselectivities.…”

Section: Synthesis Of N S Heterocyclesmentioning

confidence: 99%

Recent Advances in N‐Heterocyclic Carbene Catalyzed Oxidative Cyclization for the Formation of Heterocycles

2021

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Oxidative N‐heterocyclic carbene catalyst mediated cyclization proved to be an efficient strategy for the construction of various N‐ and O‐ heterocycles. Among several metal‐free methods available for the construction of heterocyclic compounds, oxidative NHC catalysis proved to be an elegant and efficient strategy as several enantioenriched compounds with excellent enantioselectivities can be synthesized in good yields. The most common method of the generation of these heterocycles proceeds via the commonly encountered intermediate in oxidative NHC catalysis (i. e.) acyl azolium intermediate. This intermediate proves to be the active species as it can undergo reaction with suitable substrates leading to the formation of numerous N‐ and O‐ heterocycles. Herein, recent reports on different strategies that enable formal [2+2], [3+2], [3+3], [4+2] or [4+3] annulations between the incoming substrates and acyl azolium species or other active intermediates which can add to suitable substrate leading to various heterocycles were summarized.

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Enantioselective access to multi-cyclic α-amino phosphonates via carbene-catalyzed cycloaddition reactions between enals and six-membered cyclic imines

Abstract: A carbene-catalyzed enantioselective [4 + 2] cycloaddition reaction is developed and quarternary α-amino phosphonates are afforded with encouraging anti-bacterial activities.

Cited by 30 publications

References 71 publications

Hydroxy- and Amino-Phosphonates and -Bisphosphonates: Synthetic Methods and Their Biological Applications

Hydroxy- and Amino-Phosphonates and -Bisphosphonates: Synthetic Methods and Their Biological Applications

Asymmetric Synthesis of Tetrasubstituted α-Aminophosphonic Acid Derivatives

Recent Advances in N‐Heterocyclic Carbene Catalyzed Oxidative Cyclization for the Formation of Heterocycles

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