Applications of Transition‐Metal‐Catalyzed Asymmetric Allylic Substitution in Total Synthesis of Natural Products: An Update

Metal‐catalyzed asymmetric allylic substitution (AAS) reaction is one of the most synthetically useful reactions catalyzed by metal complexes for the formation of carbon‐carbon and carbon‐heteroatom bonds. It comprises the substitution of allylic substrates with a wide range of nucleophiles or SN2′‐...

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Published inChemical record Vol. 21; no. 1; pp. 29 - 68
Main Authors Mohammadkhani, Leyla, Heravi, Majid M.
Format Journal Article
LanguageEnglish
Published United States Wiley Subscription Services, Inc 01.01.2021
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Abstract Metal‐catalyzed asymmetric allylic substitution (AAS) reaction is one of the most synthetically useful reactions catalyzed by metal complexes for the formation of carbon‐carbon and carbon‐heteroatom bonds. It comprises the substitution of allylic substrates with a wide range of nucleophiles or SN2′‐type allylic substitution, which results in the formation of the above‐mentioned bonds with high levels of enantioselective induction. AAS reaction tolerates a broad range of functional groups, thus has been successfully applied in the asymmetric synthesis of a wide range of optically pure compounds. This reaction has been extensively used in the total synthesis of several complex molecules, especially natural products. In this review, we try to highlight the applications of metal (Pd, Ir, Mo, or Cu)‐catalyzed AAS reaction in the total synthesis of the biologically active natural products, as a key step, updating the subject from 2003 till date. The application of transition‐metal (Pd, Ir, Mo, or Cu)‐catalyzed asymmetric allylic substitution (AAS) reaction as an effective and powerful tool using a wide range of allylic substrates in total synthesis of natural products is reported that covers the literature from 2003 to date.
AbstractList Metal-catalyzed asymmetric allylic substitution (AAS) reaction is one of the most synthetically useful reactions catalyzed by metal complexes for the formation of carbon-carbon and carbon-heteroatom bonds. It comprises the substitution of allylic substrates with a wide range of nucleophiles or SN 2'-type allylic substitution, which results in the formation of the above-mentioned bonds with high levels of enantioselective induction. AAS reaction tolerates a broad range of functional groups, thus has been successfully applied in the asymmetric synthesis of a wide range of optically pure compounds. This reaction has been extensively used in the total synthesis of several complex molecules, especially natural products. In this review, we try to highlight the applications of metal (Pd, Ir, Mo, or Cu)-catalyzed AAS reaction in the total synthesis of the biologically active natural products, as a key step, updating the subject from 2003 till date.Metal-catalyzed asymmetric allylic substitution (AAS) reaction is one of the most synthetically useful reactions catalyzed by metal complexes for the formation of carbon-carbon and carbon-heteroatom bonds. It comprises the substitution of allylic substrates with a wide range of nucleophiles or SN 2'-type allylic substitution, which results in the formation of the above-mentioned bonds with high levels of enantioselective induction. AAS reaction tolerates a broad range of functional groups, thus has been successfully applied in the asymmetric synthesis of a wide range of optically pure compounds. This reaction has been extensively used in the total synthesis of several complex molecules, especially natural products. In this review, we try to highlight the applications of metal (Pd, Ir, Mo, or Cu)-catalyzed AAS reaction in the total synthesis of the biologically active natural products, as a key step, updating the subject from 2003 till date.
Metal‐catalyzed asymmetric allylic substitution (AAS) reaction is one of the most synthetically useful reactions catalyzed by metal complexes for the formation of carbon‐carbon and carbon‐heteroatom bonds. It comprises the substitution of allylic substrates with a wide range of nucleophiles or SN2′‐type allylic substitution, which results in the formation of the above‐mentioned bonds with high levels of enantioselective induction. AAS reaction tolerates a broad range of functional groups, thus has been successfully applied in the asymmetric synthesis of a wide range of optically pure compounds. This reaction has been extensively used in the total synthesis of several complex molecules, especially natural products. In this review, we try to highlight the applications of metal (Pd, Ir, Mo, or Cu)‐catalyzed AAS reaction in the total synthesis of the biologically active natural products, as a key step, updating the subject from 2003 till date. The application of transition‐metal (Pd, Ir, Mo, or Cu)‐catalyzed asymmetric allylic substitution (AAS) reaction as an effective and powerful tool using a wide range of allylic substrates in total synthesis of natural products is reported that covers the literature from 2003 to date.
Metal‐catalyzed asymmetric allylic substitution (AAS) reaction is one of the most synthetically useful reactions catalyzed by metal complexes for the formation of carbon‐carbon and carbon‐heteroatom bonds. It comprises the substitution of allylic substrates with a wide range of nucleophiles or S N 2′‐type allylic substitution, which results in the formation of the above‐mentioned bonds with high levels of enantioselective induction. AAS reaction tolerates a broad range of functional groups, thus has been successfully applied in the asymmetric synthesis of a wide range of optically pure compounds. This reaction has been extensively used in the total synthesis of several complex molecules, especially natural products. In this review, we try to highlight the applications of metal (Pd, Ir, Mo, or Cu)‐catalyzed AAS reaction in the total synthesis of the biologically active natural products, as a key step, updating the subject from 2003 till date.
Metal‐catalyzed asymmetric allylic substitution (AAS) reaction is one of the most synthetically useful reactions catalyzed by metal complexes for the formation of carbon‐carbon and carbon‐heteroatom bonds. It comprises the substitution of allylic substrates with a wide range of nucleophiles or SN2′‐type allylic substitution, which results in the formation of the above‐mentioned bonds with high levels of enantioselective induction. AAS reaction tolerates a broad range of functional groups, thus has been successfully applied in the asymmetric synthesis of a wide range of optically pure compounds. This reaction has been extensively used in the total synthesis of several complex molecules, especially natural products. In this review, we try to highlight the applications of metal (Pd, Ir, Mo, or Cu)‐catalyzed AAS reaction in the total synthesis of the biologically active natural products, as a key step, updating the subject from 2003 till date.
Metal-catalyzed asymmetric allylic substitution (AAS) reaction is one of the most synthetically useful reactions catalyzed by metal complexes for the formation of carbon-carbon and carbon-heteroatom bonds. It comprises the substitution of allylic substrates with a wide range of nucleophiles or S 2'-type allylic substitution, which results in the formation of the above-mentioned bonds with high levels of enantioselective induction. AAS reaction tolerates a broad range of functional groups, thus has been successfully applied in the asymmetric synthesis of a wide range of optically pure compounds. This reaction has been extensively used in the total synthesis of several complex molecules, especially natural products. In this review, we try to highlight the applications of metal (Pd, Ir, Mo, or Cu)-catalyzed AAS reaction in the total synthesis of the biologically active natural products, as a key step, updating the subject from 2003 till date.
Author Heravi, Majid M.
Mohammadkhani, Leyla
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  organization: Alzahra University Vanak
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– fundername: Iran National Science Foundation
  grantid: 9400159
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IngestDate Fri Jul 11 10:04:35 EDT 2025
Fri Jul 25 12:16:24 EDT 2025
Thu Apr 03 07:03:53 EDT 2025
Tue Jul 01 00:57:28 EDT 2025
Thu Apr 24 23:10:31 EDT 2025
Wed Jan 22 16:31:53 EST 2025
IsPeerReviewed true
IsScholarly true
Issue 1
Keywords Tsuji-Trost reaction
Asymmetric allylic substitutions
AAS
Transition-Metal-catalyzed reactions
Natural products
Total synthesis
Language English
License 2020 The Chemical Society of Japan & Wiley-VCH GmbH.
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  year: 2021
  text: January 2021
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PublicationTitle Chemical record
PublicationTitleAlternate Chem Rec
PublicationYear 2021
Publisher Wiley Subscription Services, Inc
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e_1_2_8_212_1
e_1_2_8_424_1
e_1_2_8_235_1
e_1_2_8_258_1
Helmchen G. (e_1_2_8_55_1) 2010
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e_1_2_8_310_2
e_1_2_8_10_1
e_1_2_8_56_1
e_1_2_8_356_1
e_1_2_8_33_2
e_1_2_8_310_3
e_1_2_8_333_1
e_1_2_8_102_1
e_1_2_8_148_1
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e_1_2_8_125_1
e_1_2_8_379_1
e_1_2_8_24_2
e_1_2_8_47_2
e_1_2_8_224_2
e_1_2_8_247_2
e_1_2_8_201_1
e_1_2_8_247_1
e_1_2_8_345_1
e_1_2_8_368_1
e_1_2_8_138_2
e_1_2_8_322_2
e_1_2_8_115_1
e_1_2_8_13_2
e_1_2_8_59_2
e_1_2_8_190_1
e_1_2_8_36_2
e_1_2_8_213_2
e_1_2_8_259_1
e_1_2_8_423_1
e_1_2_8_236_1
e_1_2_8_311_1
e_1_2_8_334_1
e_1_2_8_357_1
e_1_2_8_149_1
e_1_2_8_103_1
e_1_2_8_126_1
e_1_2_8_69_2
e_1_2_8_180_1
e_1_2_8_202_2
e_1_2_8_225_2
e_1_2_8_116_2
e_1_2_8_139_2
e_1_2_8_192_1
e_1_2_8_323_2
e_1_2_8_346_1
e_1_2_8_300_2
e_1_2_8_369_2
e_1_2_8_369_1
Kazmaier U. (e_1_2_8_404_1) 2011
e_1_2_8_35_1
e_1_2_8_191_1
e_1_2_8_237_2
e_1_2_8_422_1
e_1_2_8_214_2
e_1_2_8_410_1
e_1_2_8_104_2
e_1_2_8_127_1
e_1_2_8_335_1
e_1_2_8_12_1
e_1_2_8_312_1
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SSID ssj0011477
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Snippet Metal‐catalyzed asymmetric allylic substitution (AAS) reaction is one of the most synthetically useful reactions catalyzed by metal complexes for the formation...
Metal-catalyzed asymmetric allylic substitution (AAS) reaction is one of the most synthetically useful reactions catalyzed by metal complexes for the formation...
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SubjectTerms AAS
Asymmetric allylic substitutions
Asymmetric synthesis
Asymmetry
Biological activity
Carbon
Chemical reactions
Chemical synthesis
Coordination compounds
Copper
Enantiomers
Functional groups
Metal complexes
Natural products
Nucleophiles
Palladium
Substitution reactions
Substrates
Total synthesis
Transition-Metal-catalyzed reactions
Tsuji-Trost reaction
Title Applications of Transition‐Metal‐Catalyzed Asymmetric Allylic Substitution in Total Synthesis of Natural Products: An Update
URI https://onlinelibrary.wiley.com/doi/abs/10.1002%2Ftcr.202000086
https://www.ncbi.nlm.nih.gov/pubmed/33206466
https://www.proquest.com/docview/2479403589
https://www.proquest.com/docview/2461856538
Volume 21
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