通过 II 型阴离子接力化学，实现 2,4,6-三取代哌啶的多样性导向合成。
Diversity-oriented synthesis of 2,4,6-trisubstituted piperidines via type II anion relay chemistry.
机构信息
Department of Chemistry, University of Pennsylvania, Philadelphia, Pennsylvania 19104, USA.
出版信息
Org Lett. 2011 Jul 1;13(13):3328-31. doi: 10.1021/ol2010598. Epub 2011 Jun 6.
Abstract
An effective, general protocol for the Diversity-Oriented Synthesis (DOS) of 2,4,6-trisubstituted piperidine congeners has been designed and validated. The successful strategy entails a modular approach to all possible stereoisomers of the selected piperidine scaffold, exploiting Type II Anion Relay Chemistry (ARC), followed in turn by intramolecular S(N)2 cyclization, chemoselective removal of the dithiane moieties and carbonyl reductions.
摘要
已设计并验证了一种用于 2,4,6-三取代哌啶同系物的定向多样性合成（DOS）的有效、通用方案。该成功策略需要采用模块化方法来处理所选哌啶骨架的所有可能的立体异构体，利用 II 型阴离子接力化学（ARC），随后进行分子内 S(N)2 环化、选择性去除二硫杂环戊烷部分和羰基还原。
相似文献
1
Diversity-oriented synthesis of 2,4,6-trisubstituted piperidines via type II anion relay chemistry.通过 II 型阴离子接力化学，实现 2,4,6-三取代哌啶的多样性导向合成。
Org Lett. 2011 Jul 1;13(13):3328-31. doi: 10.1021/ol2010598. Epub 2011 Jun 6.
2
Anion Relay Chemistry: Development of an Effective Diastereoselective [3+2] Annulation Tactic Exploiting an Aldol/Brook Rearrangement/Cyclization Cascade.阴离子接力化学：开发有效的非对映选择性[3+2]环加成策略，利用醛醇/ Brook 重排/环化级联反应
Angew Chem Int Ed Engl. 2017 Nov 6;56(45):14102-14106. doi: 10.1002/anie.201708017. Epub 2017 Oct 10.
3
Stereoselective synthesis of 2,4,5-trisubstituted piperidines via radical cyclization.通过自由基环化反应立体选择性合成 2,4,5-三取代哌啶。
J Org Chem. 2010 Nov 5;75(21):7347-57. doi: 10.1021/jo101631y.
4
Asymmetric synthesis of 2,4,5-trisubstituted piperidines from sulfinimine-derived delta-amino beta-ketoesters. Formal synthesis of pseudodistomin B triacetate.由亚磺酰亚胺衍生的δ-氨基β-酮酯不对称合成2,4,5-三取代哌啶。伪扭曲菌素B三乙酸酯的形式合成。
J Org Chem. 2005 Jul 8;70(14):5413-9. doi: 10.1021/jo050373o.
5
Au-catalyzed piperidine synthesis via tandem acyloxy migration/intramolecular [3 + 2] cycloaddition of enynyl esters.金催化的通过酰氧基迁移/炔基酯的分子内[3 + 2]环加成的哌啶合成。
Org Lett. 2011 Dec 16;13(24):6448-51. doi: 10.1021/ol202746s. Epub 2011 Nov 15.
6
A regio- and diastereoselective intramolecular nitrone cycloaddition for practical 3- and 2,3-disubstituted piperidine synthesis from gamma-butyrolactone.一种用于从γ-丁内酯实际合成3-和2,3-二取代哌啶的区域和非对映选择性分子内硝酮环加成反应。
J Org Chem. 2009 Jan 2;74(1):254-63. doi: 10.1021/jo8018285.
7
Chemoenzymatic synthesis of all four diastereomers of 2,6-disubstituted piperidines through stereoselective monoamination of 1,5-diketones.通过 1,5-二酮的立体选择性单胺化反应，全合成所有四个立体异构体的 2,6-二取代哌啶。
Chemistry. 2013 Feb 18;19(8):2859-65. doi: 10.1002/chem.201202793. Epub 2013 Jan 4.
8
[1,5]-Anion relay via intramolecular proton transfer to generate 3,3-bis(silyl) allyloxy lithium: a useful scaffold for syn-addition to aldehydes and ketones.[1,5]-通过分子内质子转移生成 3,3-双（硅基）烯丙氧基锂的阴离子接力：用于与醛和酮进行 syn-加成的有用支架。
Org Lett. 2014 Feb 21;16(4):1084-7. doi: 10.1021/ol4036402. Epub 2014 Feb 5.
9
A highly stereoselective synthesis of (-)-(ent)-julifloridine from the cyclization of an alanine-derived chloroamine with an acetylenic sulfone.通过丙氨酸衍生的氯胺与炔基砜的环化反应实现(-)-(对映体)-朱利弗洛里定的高度立体选择性合成。
J Org Chem. 2007 May 11;72(10):3853-8. doi: 10.1021/jo0703101. Epub 2007 Apr 17.
10
Type II Anion Relay Chemistry: Exploiting Bifunctional Weinreb Amide Linchpins for the One-Pot Synthesis of Differentiated 1,3-Diketones, Pyrans, and Spiroketals.II型阴离子接力化学：利用双功能Weinreb酰胺关键中间体进行一锅法合成结构各异的1,3-二酮、吡喃和螺缩酮。
Angew Chem Int Ed Engl. 2016 Jan 4;55(1):232-5. doi: 10.1002/anie.201509342. Epub 2015 Nov 20.
引用本文的文献
1
Synthetic Access to the Mandelalide Family of Macrolides: Development of an Anion Relay Chemistry Strategy.合成曼德林内酯类大环内酯家族的方法学研究：阴离子接力化学策略的发展。
J Org Chem. 2018 Apr 20;83(8):4287-4306. doi: 10.1021/acs.joc.8b00268. Epub 2018 Feb 26.
2
Anion Relay Chemistry: Development of an Effective Diastereoselective [3+2] Annulation Tactic Exploiting an Aldol/Brook Rearrangement/Cyclization Cascade.阴离子接力化学：开发有效的非对映选择性[3+2]环加成策略，利用醛醇/ Brook 重排/环化级联反应
Angew Chem Int Ed Engl. 2017 Nov 6;56(45):14102-14106. doi: 10.1002/anie.201708017. Epub 2017 Oct 10.
3
Stereoselective Tandem Bis-Electrophile Couplings of Diborylmethane.二硼甲烷的立体选择性串联双亲电偶联反应。
J Am Chem Soc. 2017 Oct 11;139(40):14061-14064. doi: 10.1021/jacs.7b09309. Epub 2017 Sep 27.
4
Synthesis of cyclic 1,3-diols as scaffolds for spatially directed libraries.环状1,3 -二醇作为空间定向文库支架的合成。
Org Biomol Chem. 2016 May 14;14(18):4299-303. doi: 10.1039/c6ob00598e.
5
Total Synthesis of (-)-Secu'amamine A Exploiting Type II Anion Relay Chemistry.利用II型阴离子接力化学全合成（-）-西卡胺A
Org Lett. 2015 Sep 4;17(17):4232-5. doi: 10.1021/acs.orglett.5b02018. Epub 2015 Aug 20.
6
Reversed-Polarity Synthesis of Diaryl Ketones through Palladium-Catalyzed Direct Arylation of 2-Aryl-1,3-dithianes.通过钯催化的2-芳基-1,3-二硫杂环戊烷直接芳基化反应实现二芳基酮的反极性合成
Adv Synth Catal. 2014 Nov 24;356(17):3659-3667. doi: 10.1002/adsc.201400695.
7
A unified synthetic strategy to the Cryptocarya family of natural products exploiting Anion Relay Chemistry (ARC).利用阴离子接力化学（ARC）对Cryptocarya 族天然产物的统一综合策略。
Org Lett. 2013 May 3;15(9):2282-5. doi: 10.1021/ol400857k. Epub 2013 Apr 24.
8
Long-range anion relay chemistry (LR-ARC): a validated ARC tactic.长程阴离子接力化学（LR-ARC）：一种经过验证的 ARC 策略。
Org Lett. 2012 Dec 21;14(24):6314-7. doi: 10.1021/ol303080h. Epub 2012 Dec 6.
9
Anion relay chemistry: access to the type II ARC reaction manifold through a fundamentally different reaction pathway exploiting 1-oxa-2-silacyclopentanes and related congeners.阴离子接力化学：通过利用1-氧杂-2-硅杂环戊烷及相关同系物的根本不同的反应途径进入II型ARC反应体系。
Angew Chem Int Ed Engl. 2011 Sep 12;50(38):8904-7. doi: 10.1002/anie.201103886. Epub 2011 Aug 10.
本文引用的文献
1
Diversity-oriented synthesis leads to an effective class of bifunctional linchpins uniting anion relay chemistry (ARC) with benzyne reactivity.导向多样性合成得到了一类有效的双功能链接子，它将阴离子接力化学（ARC）与苯炔反应性结合在一起。
Proc Natl Acad Sci U S A. 2011 Apr 26;108(17):6787-92. doi: 10.1073/pnas.1015265108. Epub 2011 Jan 18.
2
A modular, efficient, and stereoselective synthesis of substituted piperidin-4-ols.一种取代哌啶-4-醇的模块化、高效且立体选择性合成方法。
Angew Chem Int Ed Engl. 2010 Nov 22;49(48):9178-81. doi: 10.1002/anie.201004712.
3
Benzyl and phenylthiomethyl silanes: a new class of bifunctional linchpins for type II anion relay chemistry (ARC).苄基和苯硫甲基硅烷：II 型阴离子中继化学 (ARC) 的新一类双功能连接子。
Org Lett. 2010 Mar 19;12(6):1260-3. doi: 10.1021/ol100130x.
4
Uniting anion relay chemistry with Pd-mediated cross coupling: design, synthesis and evaluation of bifunctional aryl and vinyl silane linchpins.将阴离子接力化学与 Pd 介导的交叉偶联相结合：双功能芳基和乙烯基硅烷连接子的设计、合成和评价。
Org Lett. 2010 Feb 5;12(3):588-91. doi: 10.1021/ol902784q.
5
Stereoselective synthesis of 2,6-disubstituted piperidines using the iridium-catalyzed allylic cyclization as configurational switch: asymmetric total synthesis of (+)-241 d and related piperidine alkaloids.以铱催化的烯丙基环化作为构型转换的2,6-二取代哌啶的立体选择性合成：(+)-241 d及相关哌啶生物碱的不对称全合成
Chemistry. 2009;15(9):2050-4. doi: 10.1002/chem.200802525.
6
Evolution of multi-component anion relay chemistry (ARC): construction of architecturally complex natural and unnatural products.多组分阴离子中继化学（ARC）的发展：构建结构复杂的天然和非天然产物。
Chem Commun (Camb). 2008 Dec 7(45):5883-95. doi: 10.1039/b810394a. Epub 2008 Sep 30.
7
Ortho-TMS benzaldehyde: an effective linchpin for type II anion relay chemistry (ARC).邻位三甲基硅基苯甲醛：II型阴离子接力化学（ARC）的有效关键物质。
Angew Chem Int Ed Engl. 2008;47(37):7082-6. doi: 10.1002/anie.200802301.
8
Discovery of 2,4,6-trisubstituted N-arylsulfonyl piperidines as gamma-secretase inhibitors.发现2,4,6-三取代的N-芳基磺酰基哌啶作为γ-分泌酶抑制剂
Bioorg Med Chem Lett. 2007 Nov 15;17(22):6290-4. doi: 10.1016/j.bmcl.2007.09.006. Epub 2007 Sep 7.
9
A general, convergent strategy for the construction of indolizidine alkaloids: total syntheses of (-)-indolizidine 223AB and alkaloid (-)-205B.一种构建吲哚里西啶生物碱的通用、收敛策略：（-）-吲哚里西啶223AB和生物碱（-）-205B的全合成。
J Org Chem. 2006 Mar 31;71(7):2547-57. doi: 10.1021/jo052314g.
10
Stereoselective synthesis of 2,4,5-trisubstituted piperidines by carbonyl ene and Prins cyclisations.通过羰基烯反应和普林斯环化反应立体选择性合成2,4,5-三取代哌啶
Org Biomol Chem. 2006 Jan 7;4(1):51-3. doi: 10.1039/b515547a. Epub 2005 Nov 29.
Zotero 插件