A convenient and practical method for the synthesis of <i>N</i>‐thiophosphoryl aldimines and ketimines

Xu, Xinyuan; Wang, Chungui; Zhou, Zhenghong; Zeng, Zebing; Ma, Xinpeng; Zhao, Guofeng; Tang, Chuchi

doi:10.1002/hc.20412

Cited by 60 publications

(7 citation statements)

References 19 publications

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“…N-Thiophosphinoyl ketimines also allow exceptional copper(I) catalysts to catalyze asymmetric nucleophilic conditions [95]. In 2013, Shibasaki and co-workers [96] reported the synthesis of asymmetric addition of dialkyl phosphite to N-thiophosphinoyl ketimines using copper(I)-catalyst to afford 90% to 96% yields.…”

Section: Synthesis Of Biologically Active Phosphine Sulfidesmentioning

confidence: 99%

A Focused Review of Synthetic Applications of Lawesson’s Reagent in Organic Synthesis

Khatoon

Abdulmalek

2021

Molecules

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Lawesson’s reagent (LR) is a well-known classic example of a compound with unique construction and unusual chemical behavior, with a wide range of applications in synthetic organic chemistry. Its main functions were rounded for the thionation of various carbonyl groups in the early days, with exemplary results. However, the role of Lawesson’s reagent in synthesis has changed drastically, and now its use can help the chemistry community to understand innovative ideas. These include constructing biologically valuable heterocycles, coupling reactions, and the thionation of natural compounds. The ease of availability and the convenient usage of LR as a thionating agent made us compile a review on the new diverse applications on some common functional groups, such as ketones, esters, amides, alcohols, and carboxylic acids, with biological applications. Since the applications of LR are now diverse, we have also included some new classes of heterocycles such as thiazepines, phosphine sulfides, thiophenes, and organothiophosphorus compounds. Thionation of some biologically essential steroids and terpenoids has also been compiled. This review discusses the recent insights into and synthetic applications of this famous reagent from 2009 to January 2021.

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Section: Synthesis Of Biologically Active Phosphine Sulfidesmentioning

confidence: 99%

A Focused Review of Synthetic Applications of Lawesson’s Reagent in Organic Synthesis

Khatoon

Abdulmalek

2021

Molecules

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“…This disparity was ascribed to the fact that the ortho substituent compromised a six‐membered cyclic transition state with in situ‐generated ( Z )‐enolate, leading to give the anti product through an open transition state. For the Mannich‐type reaction, soft Lewis basic N ‐thiophosphinoylimines 38 proved best among a series of imines in terms of stereoselectivity . A catalyst comprising the chiral soft Lewis acid Cu I /( R )‐xyl‐Segphos 39 and Barton's base performed optimally to predominantly give anti ‐Mannich adducts 40 , which were directly hydrolyzed under acidic conditions (6 n HCl aq., 80 °C) to produce enantioenriched β‐amino acids with α‐azido functionality 41 .…”

Section: Enantioselective C−c Bond Formation By Direct Enolization Ofmentioning

confidence: 99%

Nucleophilic and Electrophilic Activation of Non‐Heteroaromatic Amides in Atom‐Economical Asymmetric Catalysis

Kumagai

Shibasaki

2016

Chemistry A European J

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Recent advances in catalytic asymmetric carbon-carbon bond-forming reactions of non-heteroaromatic amide substrates are highlighted. Among carbonyl compounds, amides have received limited attention in catalytic asymmetric transformations mainly owing to their lower reactivity. Amides are reluctant to form enolates for nucleophilic addition, and α,β-unsaturated amides exhibit diminished electrophilicity at the β-carbon. Recent advances in asymmetric catalysis rendered these amides amenable to enantioselective reactions with perfect atom economy, producing synthetically useful chiral building blocks. This Minireview summarizes recent developments in the field.

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“…For aromatic aldehydes,t he presence or absence of an ortho substituent wasc onsidered as the determinant for anti/syn diastereoselectivity.T his disparity was ascribed to the fact that the ortho substituent compromised as ix-membered cyclic transition state with in situ-generated (Z)-enolate, leading to give the anti product through an open transition state. For the Mannich-type reaction, soft Lewis basic N-thiophosphinoylimines 38 [27] provedb est among as eries of iminesi n terms of stereoselectivity. [25b] Ac atalystc omprising the chiral soft Lewis acid Cu I /(R)-xyl-Segphos 39 and Barton's base performed optimally to predominantly give anti-Mannicha dducts 40,w hich were directly hydrolyzed under acidic conditions (6 n HCl aq.,8 08C) to produce enantioenriched b-amino acids with a-azido functionality 41.…”

Section: -Azaindoline Amidesmentioning

confidence: 99%

ChemInform Abstract: Nucleophilic and Electrophilic Activation of Non‐Heteroaromatic Amides in Atom‐Economical Asymmetric Catalysis

Kumagai

Shibasaki

2016

ChemInform

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A convenient and practical method for the synthesis of N‐thiophosphoryl aldimines and ketimines

Abstract: A convenient and practical method for the preparation of N-thiophosphoryl imines was developed through the thermal condensation of acetals with different thiophosphoramides at

Cited by 60 publications

References 19 publications

A Focused Review of Synthetic Applications of Lawesson’s Reagent in Organic Synthesis

A Focused Review of Synthetic Applications of Lawesson’s Reagent in Organic Synthesis

Nucleophilic and Electrophilic Activation of Non‐Heteroaromatic Amides in Atom‐Economical Asymmetric Catalysis

ChemInform Abstract: Nucleophilic and Electrophilic Activation of Non‐Heteroaromatic Amides in Atom‐Economical Asymmetric Catalysis

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