دورية أكاديمية
أعرض في EDS

Chiral donor-acceptor azetines as powerful reactants for synthesis of amino acid derivatives.

التفاصيل البيبلوغرافية
العنوان: Chiral donor-acceptor azetines as powerful reactants for synthesis of amino acid derivatives.
المؤلفون: Marichev KO; Department of Chemistry, The University of Texas at San Antonio, San Antonio, TX, 78249, USA., Dong K; Department of Chemistry, The University of Texas at San Antonio, San Antonio, TX, 78249, USA., Massey LA; Department of Chemistry, The University of Texas at San Antonio, San Antonio, TX, 78249, USA., Deng Y; Department of Chemistry, The University of Texas at San Antonio, San Antonio, TX, 78249, USA., De Angelis L; Department of Chemistry, The University of Texas at San Antonio, San Antonio, TX, 78249, USA., Wang K; Department of Chemistry, The University of Texas at San Antonio, San Antonio, TX, 78249, USA., Arman H; Department of Chemistry, The University of Texas at San Antonio, San Antonio, TX, 78249, USA., Doyle MP; Department of Chemistry, The University of Texas at San Antonio, San Antonio, TX, 78249, USA. michael.doyle@utsa.edu.
المصدر: Nature communications [Nat Commun] 2019 Nov 22; Vol. 10 (1), pp. 5328. Date of Electronic Publication: 2019 Nov 22.
نوع المنشور: Journal Article; Research Support, Non-U.S. Gov't; Research Support, U.S. Gov't, Non-P.H.S.
اللغة: English
بيانات الدورية: Publisher: Nature Pub. Group Country of Publication: England NLM ID: 101528555 Publication Model: Electronic Cited Medium: Internet ISSN: 2041-1723 (Electronic) Linking ISSN: 20411723 NLM ISO Abbreviation: Nat Commun Subsets: MEDLINE
أسماء مطبوعة: Original Publication: [London] : Nature Pub. Group
مواضيع طبية MeSH: Azetines/*chemical synthesis , Cycloaddition Reaction/*methods, Amino Acids ; Azetidines ; Catalysis ; Chemistry Techniques, Synthetic/methods ; Diazonium Compounds ; Indicators and Reagents/chemical synthesis ; Stereoisomerism
مستخلص: Coupling reactions of amines and alcohols are of central importance for applications in chemistry and biology. These transformations typically involve the use of a reagent, activated as an electrophile, onto which nucleophile coupling results in the formation of a carbon-nitrogen or a carbon-oxygen bond. Several promising reagents and procedures have been developed to achieve these bond forming processes in high yields with excellent stereocontrol, but few offer direct coupling without the intervention of a catalyst. Herein, we report the synthesis of chiral donor-acceptor azetines by highly enantioselective [3 + 1]-cycloaddition of enoldiazoacetates with aza-ylides and their selective coupling with nitrogen and oxygen nucleophiles via 3-azetidinones to form amino acid derivatives, including those of peptides and natural products. The overall process is general for a broad spectrum of nucleophiles, has a high degree of electronic and steric selectivity, and retains the enantiopurity of the original azetine.
References: Angew Chem Int Ed Engl. 2010 Apr 6;49(16):2900-3. (PMID: 20235261)
J Am Chem Soc. 2017 Mar 1;139(8):3209-3226. (PMID: 28140573)
Org Lett. 2015 Feb 20;17(4):790-3. (PMID: 25666863)
J Am Chem Soc. 1967 Jun 1;89(12):3020-6. (PMID: 27525566)
Org Lett. 2010 May 7;12(9):1944-7. (PMID: 20356106)
Angew Chem Int Ed Engl. 2012 Sep 24;51(39):9829-33. (PMID: 22945294)
Angew Chem Int Ed Engl. 2016 Aug 16;55(34):10108-12. (PMID: 27391211)
ACS Chem Biol. 2014 Apr 18;9(4):855-66. (PMID: 24579725)
J Agric Food Chem. 2018 Mar 14;66(10):2324-2333. (PMID: 27794602)
Org Lett. 2014 Feb 7;16(3):856-9. (PMID: 24410016)
Angew Chem Int Ed Engl. 2019 Mar 11;58(11):3589-3593. (PMID: 30600592)
Angew Chem Int Ed Engl. 2011 Sep 26;50(40):9370-3. (PMID: 21948433)
J Org Chem. 2008 Jul 18;73(14):5481-8. (PMID: 18549273)
J Am Chem Soc. 2012 Nov 7;134(44):18241-4. (PMID: 23098215)
Chem Rev. 2002 Jan;102(1):29-60. (PMID: 11782128)
Angew Chem Int Ed Engl. 2014 May 26;53(22):5639-42. (PMID: 24719367)
Org Lett. 2008 Aug 21;10(16):3525-6. (PMID: 18630921)
ACS Chem Biol. 2008 Mar 20;3(3):142-55. (PMID: 18355003)
Chemistry. 2012 Jul 23;18(30):9221-4. (PMID: 22730267)
Chem Rev. 2010 May 12;110(5):2620-40. (PMID: 20000749)
Nat Chem. 2019 Feb;11(2):117-122. (PMID: 30532013)
Angew Chem Int Ed Engl. 2016 Sep 19;55(39):11867-71. (PMID: 27539065)
Chemistry. 2017 Jan 1;23(1):61-64. (PMID: 27790762)
Planta Med. 2019 Jan;85(1):48-55. (PMID: 30308694)
Acc Chem Res. 2006 Oct;39(10):721-8. (PMID: 17042472)
Chem Commun (Camb). 2013 Nov 11;49(87):10287-9. (PMID: 24061600)
J Am Chem Soc. 2011 Jun 8;133(22):8470-3. (PMID: 21557577)
Chem Commun (Camb). 2015 Aug 21;51(65):12924-7. (PMID: 26186132)
Chem Rev. 2005 Feb;105(2):395-424. (PMID: 15700950)
J Am Chem Soc. 2019 Mar 20;141(11):4573-4578. (PMID: 30836746)
Chem Soc Rev. 2009 Dec;38(12):3348-59. (PMID: 20449054)
Bioorg Med Chem. 2018 Jun 1;26(10):2816-2826. (PMID: 29042225)
Angew Chem Int Ed Engl. 2012 Jun 11;51(24):5900-3. (PMID: 22566213)
Science. 2016 Jan 15;351(6270):241-6. (PMID: 26816372)
J Org Chem. 2014 Jul 3;79(13):6189-95. (PMID: 24885772)
Org Lett. 2017 Oct 20;19(20):5681-5684. (PMID: 28976769)
Angew Chem Int Ed Engl. 2017 Jun 19;56(26):7479-7483. (PMID: 28493594)
Biochemistry. 2010 Feb 23;49(7):1364-76. (PMID: 20102226)
Tetrahedron. 2012 Dec 30;68(52):10640-10664. (PMID: 23264702)
Angew Chem Int Ed Engl. 2010 May 3;49(20):3524-7. (PMID: 20544904)
المشرفين على المادة: 0 (2-azetidinone)
0 (Amino Acids)
0 (Azetidines)
0 (Azetines)
0 (Diazonium Compounds)
0 (Indicators and Reagents)
تواريخ الأحداث: Date Created: 20191124 Date Completed: 20200302 Latest Revision: 20210110
رمز التحديث: 20240628
مُعرف محوري في PubMed: PMC6874555
DOI: 10.1038/s41467-019-13326-8
PMID: 31757976
قاعدة البيانات: MEDLINE
الوصف
تدمد:2041-1723
DOI:10.1038/s41467-019-13326-8