Enantioselective Synthesis of Cyclic α‐Aminophosphonates through N‐Heterocyclic Carbene‐Catalyzed [4+2] Annulation of Enals with α‐Iminophosphonates

Luo, Zhi; Gao, Zhong‐Hua; Zhang, Chunlin; Chen, Kun‐Quan; Ye, Song

doi:10.1002/ajoc.201800604

Cited by 11 publications

(4 citation statements)

References 45 publications

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“…The reaction products were obtained in moderate to excellent yield (51–96%) and enantioselectivities above 92%. Remarkably, simultaneously to Chi’s work, Ye and colleagues reported the same transformation in similar reaction conditions with a different NHC catalyst, resulting in the formation of the opposite enantiomer of α-aminophosphonates 231 and 232 [ 88 ].…”

Section: Enantioselective Synthesis Of Tetrasubstituted α-Aminophosphonic Acid Derivativesmentioning

confidence: 92%

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: Enantioselective Synthesis Of Tetrasubstituted α-Aminophosphonic Acid Derivativesmentioning

confidence: 92%

Asymmetric Synthesis of Tetrasubstituted α-Aminophosphonic Acid Derivatives

et al. 2021

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“…In addition, they reported that imine 42 can also be in situ prepared from cyclic α‐aminophosphonates 12 (Scheme ) and then react with substituted crotonaldehydes 50 in the presence of four equivalents of the oxidant agent, to afford α‐aminophosphonates 52 in lower yields (36–51%), but without losing enantioselectivity. By the same time, Ye reported a similar process using one equivalent of cesium carbonate as a base, instead of sodium acetate …”

Section: Enantioselective Reactions With α‐Iminophosphonatesmentioning

confidence: 94%

“…By the same time, Ye reported a similar process using one equivalent of cesium carbonate as a base, instead of sodium acetate. [45] Scheme 18. Palladium catalyzed enantioselective arylation of cyclic αketiminophosphonates.…”

Section: Nucleophilic Addition To Cyclic Ketiminesmentioning

confidence: 99%

α‐Iminophosphonates: Useful Intermediates for Enantioselective Synthesis of α‐Aminophosphonates

et al. 2020

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A wide range of methods for the enantioselective synthesis of α‐aminophosphonic acid derivatives have been developed over the years. Although the most used methodology is the Pudovik reaction, the use of α‐iminophosphonates for the synthesis of optically active α‐aminophosphonates has emerged during the last years. The existing methods for the synthesis of α‐phosphorylated imines and their enantioselective reactions for the synthesis of enantio‐enriched α‐aminophosphonates are summarized in this review.

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“…The chiral phosphoric acid catalyst (PA5) was synthesized according to the established literature procedure. 18 Cyclic imines 1 were synthesized from salicylaldehyde by the slightly modified literature procedure. 19 The indolizines 2 were prepared according to the procedure described in literature.…”

Section: ■ Experimental Sectionmentioning

confidence: 99%

Chiral Phosphoric Acid-Catalyzed Asymmetric Friedel–Crafts Addition of Indolizine to Cyclic N-Sulfonyl Imine

Subba,

Sadhu,

Singh

2023

J. Org. Chem.

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A highly efficient chiral phosphoric acid-catalyzed enantioselective Friedel−Crafts addition of indolizine to cyclic Nsulfonyl imine has been established. The newly developed protocol, which probably proceeds via a monoactivation reaction pathway, allows the access of enantioenriched sulfonamide functionalized indolizines with excellent yields (up to 99%) and enantioselectivities (up to 99%). Moreover, the synthetic utility of this protocol has been explored with some chemical transformations.

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Enantioselective Synthesis of Cyclic α‐Aminophosphonates through N‐Heterocyclic Carbene‐Catalyzed [4+2] Annulation of Enals with α‐Iminophosphonates

Abstract: The N-heterocyclic carbene-catalyzed [4 + 2] annulation of enals with α-iminophosphonates was developed to give the corresponding cyclic α-aminophosphonates in high yields with excellent enantioselectivities.

Cited by 11 publications

References 45 publications

Asymmetric Synthesis of Tetrasubstituted α-Aminophosphonic Acid Derivatives

Asymmetric Synthesis of Tetrasubstituted α-Aminophosphonic Acid Derivatives

α‐Iminophosphonates: Useful Intermediates for Enantioselective Synthesis of α‐Aminophosphonates

Chiral Phosphoric Acid-Catalyzed Asymmetric Friedel–Crafts Addition of Indolizine to Cyclic N-Sulfonyl Imine

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