Asymmetric synthesis of conformationally constrained L-AP4 analogues using chiral sulfinyl auxiliary

Midura, Wanda H.; Krysiak, Joanna; Rzewnicka, Aneta; Supeł, Anna; Łyżwa, P.; Ewas, Ashraf M.

doi:10.1016/j.tet.2012.10.085

Cited by 17 publications

(11 citation statements)

References 27 publications

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“…In a similar fashion, Midura et al . prepared these chiral phosphono‐cyclopropyl glycine (PCG) derivatives by the use of a chiral sulfinyl auxiliary (Scheme 84b) [173] . Enantiopure phosphono‐cyclopropanyl ester 239 was obtained via a cyclopropanation reaction of chiral vinyl sulfoxide with ethyl (dimethyl‐sulfuranylidene) acetate (EDSA) in 12:1 dr.…”

Section: Asymmetric Construction Of Cyclopropane and Bicyclo‐[xyz]‐mentioning

confidence: 99%

Asymmetric Synthesis of Chiral Amino Carboxylic‐Phosphonic Acid Derivatives

Cahard

Cao

et al. 2020

Adv Synth Catal

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Chiral amino acids featuring a phosphonate pendant arm are an important type of biologically active scaffold. Here in this review, we comprehensively summarize the modern synthetic methods towards asymmetric construction of chiral amino carboxylic‐phosphonic acid derivatives. The main streams of such interesting compounds include phosphono‐containing α‐, β‐, and γ‐amino acid derivatives, amino acid fluorophosphonate derivatives, amino acid cyclopropanylphosphonate derivatives, and bisphosphono‐amino acid derivatives. Chiral resolution protocols, chiral auxiliary‐directed syntheses, and valorization of the pool of abundant chiral amino acid resources remain contemporary concerns, and meanwhile catalytic enantioselective synthesis has also emerged as a potent strategy as demonstrated by the latest advances.magnified image

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Section: Asymmetric Construction Of Cyclopropane and Bicyclo‐[xyz]‐mentioning

confidence: 99%

Asymmetric Synthesis of Chiral Amino Carboxylic‐Phosphonic Acid Derivatives

Cahard

Cao

et al. 2020

Adv Synth Catal

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“…35 The stereogenic centers in cyclopropane ring were formed under sulfinyl group control, in asymmetric cyclopropanation of enantiomerically pure α-phosphoryl vinyl sulfoxides (Scheme 8). The sulfinimine-mediated asymmetric Strecker reaction allowed introduction of the amino acid moiety.…”

Section: Methodsmentioning

confidence: 99%

Recent advances on asymmetric Strecker reactions

Cai¹,

Xie²

2014

Arkivoc

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The Strecker reaction is one of the most attractive methods for the synthesis of α-amino acids and other bioactive compounds including natural products. The asymmetric Strecker reaction represents a simple and efficient method for the synthesis of optically pure α-amino acid derivatives, nucleic acids, various nitrogen and sulfur containing heterocycles and pharmaceuticals. Over the past several decades, considerable effort has been devoted towards the development of asymmetric Strecker reactions. This review provides an overview of recent asymmetric Strecker reactions, from diastereoselective reactions and catalytic enantioselective reactions including chiral catalytic metal systems and chiral organocatalytic systems.

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“…The two diastereomers are easily separable and they can be converted into enantiomerically enriched 2-(2′-phosphonocyclopropyl)glycines, that are among the most important sources of active analogues for the glutamic acid receptors. 135…”

Section: Scheme 47 Mechanism Accounting For Low Enantioselectivity Inmentioning

confidence: 99%

Asymmetric Cyclopropanation Reactions

2014

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Both physical and organic chemists are interested in the cyclopropane ring, the former owing to the strain inherent to the small ring structure, the latter prompted by the importance of this ring in naturally occurring compounds. In recent years, the increasing interest in enantioselective organic synthesis has led to a large number of papers on the preparation of cyclopropane compounds in enantioenriched form. The last review on asymmetric cyclopropanation reactions is dated 2008, thus an update is necessary with critical comparison of preparations using chiral auxiliaries, chiral metal complexes and organocatalysts. The aim of this review is an overview of these topics from 2008 to mid-2013.

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Asymmetric synthesis of conformationally constrained L-AP4 analogues using chiral sulfinyl auxiliary

Cited by 17 publications

References 27 publications

Asymmetric Synthesis of Chiral Amino Carboxylic‐Phosphonic Acid Derivatives

Asymmetric Synthesis of Chiral Amino Carboxylic‐Phosphonic Acid Derivatives

Recent advances on asymmetric Strecker reactions

Asymmetric Cyclopropanation Reactions

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