Stereocontrolled 1,3-nitrogen migration to access chiral α-amino acids

α-Amino acids are essential for life as building blocks of proteins and components of diverse natural molecules. In both industry and academia, the incorporation of unnatural amino acids is often desirable for modulating chemical, physical and pharmaceutical properties. Here we report a protocol for...

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Published inNature chemistry Vol. 14; no. 5; pp. 566 - 573
Main Authors Ye, Chen-Xi, Shen, Xiang, Chen, Shuming, Meggers, Eric
Format Journal Article
LanguageEnglish
Published London Nature Publishing Group UK 01.05.2022
NATURE PORTFOLIO
Nature Publishing Group
Subjects
639/638/403/933
639/638/549/933
639/638/549/972
639/638/77/883
Amination
Amines - chemistry
Amino acids
Amino Acids - chemistry
Analytical Chemistry
Aromatic compounds
Biochemistry
Carboxylic acids
Catalysis
Chains
Chemistry
Chemistry and Materials Science
Chemistry, Multidisciplinary
Chemistry/Food Science
Drugs
Enantiomers
Inorganic Chemistry
Natural products
Nitrogen
Nitrogen - chemistry
Nitrogenation
Optical activity
Organic Chemistry
Physical Chemistry
Physical Sciences
Reagents
Ruthenium
Science & Technology
Stereoisomerism
AMIDATION
CHEMISTRY
RUTHENIUM
IRON
CATALYST
C-H AMINATION
METAL-COMPLEXES
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Abstract α-Amino acids are essential for life as building blocks of proteins and components of diverse natural molecules. In both industry and academia, the incorporation of unnatural amino acids is often desirable for modulating chemical, physical and pharmaceutical properties. Here we report a protocol for the economical and practical synthesis of optically active α-amino acids based on an unprecedented stereocontrolled 1,3-nitrogen shift. Our method employs abundant and easily accessible carboxylic acids as starting materials, which are first connected to a nitrogenation reagent, followed by a highly regio- and enantioselective ruthenium- or iron-catalysed C( sp 3 )–H amination. This straightforward method displays a very broad scope, providing rapid access to optically active α-amino acids with aryl, allyl, propargyl and alkyl side chains, and also permits stereocontrolled late-stage amination of carboxylic-acid-containing drugs and natural products. A straightforward method for synthesizing optically active α-amino acids from abundant carboxylic acids has been developed. Based on a nitrene-mediated stereocontrolled 1,3-nitrogen shift, this approach provides access to a large variety of unnatural α-amino acids with aryl, allyl, propargyl and alkyl side chains and enables late-stage amination of carboxylic-acid-containing drugs.
AbstractList α-Amino acids are essential for life as building blocks of proteins and components of diverse natural molecules. In both industry and academia, the incorporation of unnatural amino acids is often desirable for modulating chemical, physical and pharmaceutical properties. Here we report a protocol for the economical and practical synthesis of optically active α-amino acids based on an unprecedented stereocontrolled 1,3-nitrogen shift. Our method employs abundant and easily accessible carboxylic acids as starting materials, which are first connected to a nitrogenation reagent, followed by a highly regio- and enantioselective ruthenium- or iron-catalysed C( sp 3 )–H amination. This straightforward method displays a very broad scope, providing rapid access to optically active α-amino acids with aryl, allyl, propargyl and alkyl side chains, and also permits stereocontrolled late-stage amination of carboxylic-acid-containing drugs and natural products. A straightforward method for synthesizing optically active α-amino acids from abundant carboxylic acids has been developed. Based on a nitrene-mediated stereocontrolled 1,3-nitrogen shift, this approach provides access to a large variety of unnatural α-amino acids with aryl, allyl, propargyl and alkyl side chains and enables late-stage amination of carboxylic-acid-containing drugs.
α-Amino acids are essential for life as building blocks of proteins and components of diverse natural molecules. In both industry and academia, the incorporation of unnatural amino acids is often desirable for modulating chemical, physical and pharmaceutical properties. Here we report a protocol for the economical and practical synthesis of optically active α-amino acids based on an unprecedented stereocontrolled 1,3-nitrogen shift. Our method employs abundant and easily accessible carboxylic acids as starting materials, which are first connected to a nitrogenation reagent, followed by a highly regio- and enantioselective ruthenium- or iron-catalysed C(sp )-H amination. This straightforward method displays a very broad scope, providing rapid access to optically active α-amino acids with aryl, allyl, propargyl and alkyl side chains, and also permits stereocontrolled late-stage amination of carboxylic-acid-containing drugs and natural products.
α-Amino acids are essential for life as building blocks of proteins and components of diverse natural molecules. In both industry and academia, the incorporation of unnatural amino acids is often desirable for modulating chemical, physical and pharmaceutical properties. Here we report a protocol for the economical and practical synthesis of optically active α-amino acids based on an unprecedented stereocontrolled 1,3-nitrogen shift. Our method employs abundant and easily accessible carboxylic acids as starting materials, which are first connected to a nitrogenation reagent, followed by a highly regio- and enantioselective ruthenium- or iron-catalysed C(sp3)–H amination. This straightforward method displays a very broad scope, providing rapid access to optically active α-amino acids with aryl, allyl, propargyl and alkyl side chains, and also permits stereocontrolled late-stage amination of carboxylic-acid-containing drugs and natural products.A straightforward method for synthesizing optically active α-amino acids from abundant carboxylic acids has been developed. Based on a nitrene-mediated stereocontrolled 1,3-nitrogen shift, this approach provides access to a large variety of unnatural α-amino acids with aryl, allyl, propargyl and alkyl side chains and enables late-stage amination of carboxylic-acid-containing drugs.
alpha-Amino acids are essential for life as building blocks of proteins and components of diverse natural molecules. In both industry and academia, the incorporation of unnatural amino acids is often desirable for modulating chemical, physical and pharmaceutical properties. Here we report a protocol for the economical and practical synthesis of optically active alpha-amino acids based on an unprecedented stereocontrolled 1,3-nitrogen shift. Our method employs abundant and easily accessible carboxylic acids as starting materials, which are first connected to a nitrogenation reagent, followed by a highly regio- and enantioselective ruthenium- or iron-catalysed C(sp(3))-H amination. This straightforward method displays a very broad scope, providing rapid access to optically active a-amino acids with aryl, allyl, propargyl and alkyl side chains, and also permits stereocontrolled late-stage amination of carboxylic-acid-containing drugs and natural products.
α-Amino acids are essential for life as building blocks of proteins and components of diverse natural molecules. In both industry and academia, the incorporation of unnatural amino acids is often desirable for modulating chemical, physical and pharmaceutical properties. Here we report a protocol for the economical and practical synthesis of optically active α-amino acids based on an unprecedented stereocontrolled 1,3-nitrogen shift. Our method employs abundant and easily accessible carboxylic acids as starting materials, which are first connected to a nitrogenation reagent, followed by a highly regio- and enantioselective ruthenium- or iron-catalysed C(sp3)-H amination. This straightforward method displays a very broad scope, providing rapid access to optically active α-amino acids with aryl, allyl, propargyl and alkyl side chains, and also permits stereocontrolled late-stage amination of carboxylic-acid-containing drugs and natural products.α-Amino acids are essential for life as building blocks of proteins and components of diverse natural molecules. In both industry and academia, the incorporation of unnatural amino acids is often desirable for modulating chemical, physical and pharmaceutical properties. Here we report a protocol for the economical and practical synthesis of optically active α-amino acids based on an unprecedented stereocontrolled 1,3-nitrogen shift. Our method employs abundant and easily accessible carboxylic acids as starting materials, which are first connected to a nitrogenation reagent, followed by a highly regio- and enantioselective ruthenium- or iron-catalysed C(sp3)-H amination. This straightforward method displays a very broad scope, providing rapid access to optically active α-amino acids with aryl, allyl, propargyl and alkyl side chains, and also permits stereocontrolled late-stage amination of carboxylic-acid-containing drugs and natural products.
α-Amino acids are essential for life as building blocks of proteins and components of diverse natural molecules. In both industry and academia, the incorporation of unnatural amino acids is often desirable for modulating chemical, physical, and pharmaceutical properties. We here report a protocol for the economical and practical synthesis of optically active α-amino acids based on an unprecedented stereocontrolled 1,3-nitrogen shift. Our method employs abundant and easily accessible carboxylic acids as starting materials, which are first connected to a nitrogenation reagent, followed by a highly regio- and enantioselective ruthenium- or iron-catalyzed C( sp 3 )−H amination. This straightforward method displays a very broad scope, providing rapid access to optically active α-amino acids with aryl, allyl, propargyl, and alkyl side chains, and also permits stereocontrolled late-stage amination of carboxylic acid-containing drugs and natural products.
Author Meggers, Eric
Chen, Shuming
Shen, Xiang
Ye, Chen-Xi
AuthorAffiliation 2 Department of Chemistry and Biochemistry, Oberlin College, Oberlin, Ohio 44074, United States
1 Fachbereich Chemie, Philipps-Universität Marburg, Hans-Meerwein-Strasse 4, 35043 Marburg, Germany
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  orcidid: 0000-0003-1897-2249
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  organization: Fachbereich Chemie, Philipps-Universität Marburg
BackLink https://www.ncbi.nlm.nih.gov/pubmed/35379900$$D View this record in MEDLINE/PubMed
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Issue 5
Keywords AMIDATION
CHEMISTRY
RUTHENIUM
IRON
CATALYST
C-H AMINATION
METAL-COMPLEXES
Language English
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PublicationTitle Nature chemistry
PublicationTitleAbbrev Nat. Chem
NAT CHEM
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PublicationYear 2022
Publisher Nature Publishing Group UK
NATURE PORTFOLIO
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Z Zhou (895_CR29) 2020; 6
K Ueno (895_CR31) 1976; 19
DH Ess (895_CR44) 2008; 130
A Bøgevig (895_CR4) 2002; 41
M Ju (895_CR10) 2021; 5
895_CR12
LC Morrill (895_CR7) 2012; 3
M Ichinose (895_CR22) 2011; 50
Y Zheng (895_CR27) 2017; 139
Y Liu (895_CR34) 2020; 49
H Yersin (895_CR41) 1999; 38
L-M Jin (895_CR19) 2020; 142
Z Zhou (895_CR28) 2019; 58
EH Krenske (895_CR45) 2013; 46
Y Park (895_CR9) 2017; 117
MS Chen (895_CR36) 2007; 318
T Höke (895_CR17) 2013; 49
A Nasrallah (895_CR18) 2019; 58
Y Park (895_CR25) 2019; 9
A Isidro-Llobet (895_CR48) 2009; 109
Y Nishioka (895_CR16) 2013; 52
JM Janey (895_CR3) 2005; 44
I Nägeli (895_CR11) 1997; 80
KM van Vliet (895_CR26) 2020; 10
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K Lang (895_CR24) 2019; 141
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Liang, CG (WOS:000239079900021) 2006; 45
Maestre, L (WOS:000314492500035) 2013; 135
Saghyan, AS. (000777874200002.1) 2016
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Harvey, JN (WOS:000182957600019) 2003; 238
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Park, Y (WOS:000405642800019) 2017; 117
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Morrill, LC (WOS:000304365000048) 2012; 3
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References_xml – reference: NägeliIRhodium(II)-catalyzed CH insertions with {[(4-nitrophenyl)sulfonyl]imino}phenyl-λ3-iodaneHelv. Chim. Acta1997801087110510.1002/hlca.19970800407
– reference: BauerIKnölkerH-JIron catalysis in organic synthesisChem. Rev.2015115317033871:CAS:528:DC%2BC2MXktVGktLc%3D2575171010.1021/cr500425u
– reference: van VlietKMde BruinBDioxazolones: stable substrates for the catalytic transfer of acyl nitrenesACS Catal.2020104751476910.1021/acscatal.0c009611:CAS:528:DC%2BB3cXlvFeqtb4%3D
– reference: MorrillLCLeblTSlawinAMZSmithADCatalytic asymmetric α-amination of carboxylic acids using isothioureasChem. Sci.20123208820931:CAS:528:DC%2BC38Xnt12qs7o%3D10.1039/c2sc20171b
– reference: ZalatanDNDu BoisJA chiral rhodium carboxamidate catalyst for enantioselective C–H aminationJ. Am. Chem. Soc.2008130922092211:CAS:528:DC%2BD1cXnvF2gtbk%3D18582043259718910.1021/ja8031955
– reference: YamawakiMTsutsuiHKitagakiSAnadaMHashimotoSDirhodium(II) tetrakis[N-tetrachlorophthaloyl-(S)-tert-leucinate]: a new chiral Rh(II) catalyst for enantioselective amidation of C–H bondsTetrahedron Lett.200243956195641:CAS:528:DC%2BD38Xpt1Cqtrk%3D10.1016/S0040-4039(02)02432-2
– reference: BlaskovichMATUnusual amino acids in medicinal chemistryJ. Med. Chem.20165910807108361:CAS:528:DC%2BC28XhsVKjsr7O2758934910.1021/acs.jmedchem.6b00319
– reference: LiuYIron- and cobalt-catalyzed C(sp3)–H bond functionalization reactions and their application in organic synthesisChem. Soc. Rev.202049531053581:CAS:528:DC%2BB3cXht1WjtbjO3256834010.1039/D0CS00340A
– reference: EssDHHoukKNTheory of 1,3-dipolar cycloadditions: distortion/interaction and frontier molecular orbital modelsJ. Am. Chem. Soc.200813010187101981:CAS:528:DC%2BD1cXotlGlsb8%3D1861366910.1021/ja800009z
– reference: IchinoseMEnantioselective intramolecular benzylic C–H bond amination: efficient synthesis of optically active benzosultamsAngew. Chem. Int. Ed.201150988498871:CAS:528:DC%2BC3MXhtFKhs7vK10.1002/anie.201101801
– reference: JuMSchomakerJMNitrene transfer catalysts for enantioselective C–N bond formationNat. Rev. Chem.202155805941:CAS:528:DC%2BB3MXhvVGgsbzP10.1038/s41570-021-00291-4
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– reference: ParkYChangSAsymmetric formation of γ-lactams via C–H amidation enabled by chiral hydrogen-bond-donor catalystsNat. Catal.2019921922710.1038/s41929-019-0230-x1:CAS:528:DC%2BC1MXhtFGisLfL
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– reference: SaghyanASLangerPAsymmetric Synthesis of Non-proteinogenic Amino Acids2016Wiley-VCH10.1002/9783527804498
– reference: LiangJ-LYuanS-XHuangJ-SYuW-YCheC-MHighly diastereo- and enantioselective intramolecular amidation of saturated C–H bonds catalyzed by ruthenium porphyrinsAngew. Chem. Int. Ed.200241346534681:CAS:528:DC%2BD38XnsFKntb8%3D10.1002/1521-3773(20020916)41:18<3465::AID-ANIE3465>3.0.CO;2-D
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Snippet α-Amino acids are essential for life as building blocks of proteins and components of diverse natural molecules. In both industry and academia, the...
alpha-Amino acids are essential for life as building blocks of proteins and components of diverse natural molecules. In both industry and academia, the...
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SubjectTerms 639/638/403/933
639/638/549/933
639/638/549/972
639/638/77/883
Amination
Amines - chemistry
Amino acids
Amino Acids - chemistry
Analytical Chemistry
Aromatic compounds
Biochemistry
Carboxylic acids
Catalysis
Chains
Chemistry
Chemistry and Materials Science
Chemistry, Multidisciplinary
Chemistry/Food Science
Drugs
Enantiomers
Inorganic Chemistry
Natural products
Nitrogen
Nitrogen - chemistry
Nitrogenation
Optical activity
Organic Chemistry
Physical Chemistry
Physical Sciences
Reagents
Ruthenium
Science & Technology
Stereoisomerism
Title Stereocontrolled 1,3-nitrogen migration to access chiral α-amino acids
URI https://link.springer.com/article/10.1038/s41557-022-00895-3
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https://www.ncbi.nlm.nih.gov/pubmed/35379900
https://www.proquest.com/docview/2659404421
https://www.proquest.com/docview/2647211322
https://pubmed.ncbi.nlm.nih.gov/PMC7612692
Volume 14
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