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Enantioselective one-pot synthesis of α-amino esters by a phosphine-catalyzed [3+2]-cycloaddition reaction.

作者信息

Steurer Marianne, Jensen Kim L, Worgull Dennis, Jørgensen Karl Anker

机构信息

Center for Catalysis, Department of Chemistry, Aarhus University, 8000 Aarhus C, Denmark.

出版信息

Chemistry. 2012 Jan 2;18(1):76-9. doi: 10.1002/chem.201103502. Epub 2011 Dec 7.

DOI:10.1002/chem.201103502
PMID:22162097
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC3482930/
Abstract
摘要
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/23e2/3482930/3bb510223fe0/chem0018-0076-f6.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/23e2/3482930/53adbe7ea18a/chem0018-0076-f2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/23e2/3482930/73fb30e8c8fa/chem0018-0076-f3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/23e2/3482930/87432fe59bf6/chem0018-0076-f4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/23e2/3482930/05027e250ecb/chem0018-0076-f5.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/23e2/3482930/2945a333438a/chem0018-0076-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/23e2/3482930/3bb510223fe0/chem0018-0076-f6.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/23e2/3482930/53adbe7ea18a/chem0018-0076-f2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/23e2/3482930/73fb30e8c8fa/chem0018-0076-f3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/23e2/3482930/87432fe59bf6/chem0018-0076-f4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/23e2/3482930/05027e250ecb/chem0018-0076-f5.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/23e2/3482930/2945a333438a/chem0018-0076-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/23e2/3482930/3bb510223fe0/chem0018-0076-f6.jpg

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本文引用的文献

1
Application of a new chiral phosphepine to the catalytic asymmetric synthesis of highly functionalized cyclopentenes that bear an array of heteroatom-substituted quaternary stereocenters.新型手性膦叶立德在催化不对称合成具有各种杂原子取代的季立体中心的高官能化环戊烯中的应用。
J Am Chem Soc. 2011 Aug 10;133(31):12293-7. doi: 10.1021/ja2049012. Epub 2011 Jul 18.
2
Asymmetric trienamine catalysis for the construction of structurally rigid cyclic α,α-disubstituted amino acid derivatives.用于构建结构刚性环状α,α-二取代氨基酸衍生物的不对称三烯胺催化
Chemistry. 2011 Aug 8;17(33):9032-6. doi: 10.1002/chem.201101539. Epub 2011 Jul 8.
3
通过亚苄基恶唑烷酮与联烯酸酯的形式[4+2]环化反应合成高度官能化的螺环己烯
Asian J Org Chem. 2018 Aug;7(8):1620-1625. doi: 10.1002/ajoc.201800275. Epub 2018 May 4.
4
Chiral phosphine-mediated intramolecular [3 + 2] annulation: enhanced enantioselectivity by achiral Brønsted acid.手性膦介导的分子内[3+2]环化反应:通过非手性布朗斯特酸提高对映选择性
Chem Sci. 2017 Jul 1;8(7):5196-5200. doi: 10.1039/c7sc00952f. Epub 2017 May 17.
5
Phosphine-catalyzed enantioselective [3 + 2] cycloadditions of γ-substituted allenoates with β-perfluoroalkyl enones.膦催化的γ-取代的烯丙酸酯与β-全氟烷基烯酮的对映选择性[3 + 2]环加成反应。
Chem Sci. 2017 Jun 1;8(6):4660-4665. doi: 10.1039/c7sc01432e. Epub 2017 Apr 19.
6
Nucleophilic Chiral Phosphines: Powerful and Versatile Catalysts for Asymmetric Annulations.亲核手性膦:用于不对称环化反应的强大且通用的催化剂。
Aldrichimica Acta. 2016;49(1):3-13.
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Chiral phosphines in nucleophilic organocatalysis.手性膦在亲核有机催化中的应用。
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Angew Chem Int Ed Engl. 2013 Dec 16;52(51):13616-20. doi: 10.1002/anie.201307292. Epub 2013 Nov 18.
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Beilstein J Org Chem. 2012;8:1098-104. doi: 10.3762/bjoc.8.121. Epub 2012 Jul 16.
Highly regio- and diastereoselective construction of spirocyclopenteneoxindoles through phosphine-catalyzed [3 + 2] annulation of Morita-Baylis-Hillman carbonates with isatylidene malononitriles.
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BINEPINES: chiral binaphthalene-core monophosphepine ligands for multipurpose asymmetric catalysis.双苯并[g,p]磷杂菲:用于多用途不对称催化的手性联萘并[g,p]磷杂菲配体。
Chem Soc Rev. 2011 Jul;40(7):3744-63. doi: 10.1039/c0cs00164c. Epub 2011 May 5.
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Core-structure-motivated design of a phosphine-catalyzed [3+2] cycloaddition reaction: enantioselective syntheses of spirocyclopenteneoxindoles.基于核心结构的膦催化[3+2]环加成反应设计:手性螺环戊烯氧吲哚的对映选择性合成。
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Oxazolones in organocatalysis, new tricks for an old reagent.唑酮在有机催化中的应用:老试剂的新把戏。
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Allenes as three-carbon units in catalytic cycloadditions: new opportunities with transition-metal catalysts.三碳烯作为催化环加成反应中的单元:过渡金属催化剂的新机遇。
Chemistry. 2011 Jan 10;17(2):418-28. doi: 10.1002/chem.201002366. Epub 2010 Dec 16.
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Organocatalytic enantioselective desymmetrization of cyclic enones via phosphine promoted [3+2] annulations.通过膦促进的[3+2]环加成反应实现手性催化的环状烯酮的不对称去对称化。
Chem Commun (Camb). 2011 Jan 21;47(3):1015-7. doi: 10.1039/c0cc03164j. Epub 2010 Nov 9.
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An organocatalytic [3+2] cyclisation strategy for the highly enantioselective synthesis of spirooxindoles.一种用于高对映选择性合成螺环氧化吲哚的有机催化[3+2]环化策略。
Chemistry. 2010 Nov 8;16(42):12541-4. doi: 10.1002/chem.201001791.