基于机理的六氢-2H-色烯合成方法：连续[4+2]环加成反应。
Mechanistically Inspired Route toward Hexahydro-2H-chromenes via Consecutive [4 + 2] Cycloadditions.
机构信息
Department of Chemistry, Michigan State University , East Lansing, Michigan 48824, United States.
出版信息
Org Lett. 2016 Aug 19;18(16):3976-9. doi: 10.1021/acs.orglett.6b01742. Epub 2016 Aug 3.
Abstract
Utilizing two robust C-C bond-forming reactions, the Baylis-Hillman reaction and the Diels-Alder reaction, we report a highly enantio-, regio-, and diastereoselective synthesis of hexahydro-2H-chromenes via two sequential [4 + 2] cycloadditions. These tandem and formal cycloadditions have also been performed as a "one-pot" sequence to access the corresponding heterocycles constituting up to five contiguous stereocenters in excellent yields and stereoselectivity.
摘要
利用两个强大的 C-C 键形成反应，即 Baylis-Hillman 反应和 Diels-Alder 反应，我们报告了一种通过两步[4+2]环加成反应高度对映选择性、区域选择性和非对映选择性合成六氢-2H-色烯的方法。这些串联和形式的环加成反应也可以作为“一锅法”序列进行，以获得相应的杂环，在极好的收率和立体选择性下构成多达五个连续的立体中心。
相似文献
1
Mechanistically Inspired Route toward Hexahydro-2H-chromenes via Consecutive [4 + 2] Cycloadditions.基于机理的六氢-2H-色烯合成方法：连续[4+2]环加成反应。
Org Lett. 2016 Aug 19;18(16):3976-9. doi: 10.1021/acs.orglett.6b01742. Epub 2016 Aug 3.
2
Iron-catalyzed rearrangements and cycloaddition reactions of 2H-chromenes.铁催化的 2H-色烯的重排和环加成反应。
Org Lett. 2011 Dec 16;13(24):6480-3. doi: 10.1021/ol202772k. Epub 2011 Nov 18.
3
Novel domino procedures for the synthesis of chromene derivatives and their isomerization.用于合成色烯衍生物及其异构化的新型多米诺骨牌反应过程
Mol Divers. 2016 Aug;20(3):627-38. doi: 10.1007/s11030-016-9664-0. Epub 2016 Mar 22.
4
Asymmetric synthesis of 4-amino-4H-chromenes by organocatalytic oxa-Michael/aza-Baylis-Hillman tandem reactions.通过有机催化的氧杂-迈克尔/氮杂-贝利斯-希尔曼串联反应不对称合成4-氨基-4H-色烯。
Chemistry. 2010 Aug 16;16(31):9453-6. doi: 10.1002/chem.201001293.
5
Synthesis of endo-fused 5-unsubstituted Hexahydro-2H-pyrano[3,2-c]quinolinesvia Sequential Sc(OTf)-catalyzed Cationic Imino-Diels-Alder Reaction/N-debenzylation using N-benzylanilines, 3,4-dihydro-2H-pyran and Paraformaldehyde under MW Irradiation.通过 MW 辐射下 Sc(OTf)催化的阳离子亚胺-狄尔斯-阿尔德反应/N-去苄基化反应，使用 N-苄基苯胺、3,4-二氢-2H-吡喃和多聚甲醛一锅法合成内环并[5,6]-六氢-2H-吡啶并[3,2-c]喹啉。
Curr Org Synth. 2021;18(5):431-442. doi: 10.2174/1570179418666210113160949.
6
Diversity-oriented synthesis of chromenes via metal-free domino reactions from ketones and phenols.酮和酚的无金属多组分反应导向的色烯的多样性合成。
ACS Comb Sci. 2012 Aug 13;14(8):478-83. doi: 10.1021/co3000506. Epub 2012 Jul 9.
7
Quinine-catalyzed highly enantioselective cycloannulation of o-quinone methides with malononitrile.奎宁催化邻醌甲亚胺与丙二腈的高对映选择性环加成反应。
Org Biomol Chem. 2015 Feb 28;13(8):2247-50. doi: 10.1039/c4ob02602k.
8
Highly regio- and stereoselective Diels-Alder cycloadditions via two-step and multicomponent reactions promoted by infrared irradiation under solvent-free conditions.在无溶剂条件下，通过红外辐射促进的两步反应和多组分反应实现高度区域和立体选择性的狄尔斯-阿尔德环加成反应。
Int J Mol Sci. 2012;13(3):2590-2617. doi: 10.3390/ijms13032590. Epub 2012 Feb 24.
9
Novel synthesis of 2-(trifluoromethyl)- and 2-(perfluoroalkyl)-2-hydroxy-2H-chromenes and their regiospecific reaction with silyl enol ethers.2-（三氟甲基）-和2-（全氟烷基）-2-羟基-2H-色烯的新型合成及其与硅烯醇醚的区域特异性反应。
J Org Chem. 2006 Oct 27;71(22):8637-40. doi: 10.1021/jo060765a.
10
Synthesis of functionalized 2H-1-benzopyrans by DBU-catalyzed reactions of salicylic aldehydes with allenic ketones and esters.通过DBU催化水杨酸醛与烯丙基酮和酯的反应合成功能化的2H-1-苯并吡喃。
Org Lett. 2005 Sep 29;7(20):4527-30. doi: 10.1021/ol051920v.
本文引用的文献
1
Enantioselective Amine-Catalyzed [4 + 2] Annulations of Allene Ketones and 2,3-Dioxopyrrolidine Derivatives: Synthesis of 4H-Pyran Derivatives.对映选择性胺催化的丙二烯酮与2,3-二氧代吡咯烷衍生物的[4 + 2]环化反应：4H-吡喃衍生物的合成
J Org Chem. 2015 Jul 17;80(14):7288-94. doi: 10.1021/acs.joc.5b00961. Epub 2015 Jul 2.
2
Amine-catalyzed tunable reactions of allenoates with dithioesters: formal [4+2] and [2+2] cycloadditions for the synthesis of 2,3-dihydro-1,4-oxathiines and enantioenriched thietanes.胺催化的联烯酸酯与二硫酯的可调反应：用于合成2,3-二氢-1,4-氧硫杂环己烷和对映体富集的硫杂环丙烷的形式[4+2]和[2+2]环加成反应
Chem Commun (Camb). 2015 Apr 14;51(29):6430-3. doi: 10.1039/c5cc01313e.
3
Highly enantioselective synthesis of 3,4-dihydropyrans through a phosphine-catalyzed [4+2] annulation of allenones and β,γ-unsaturated α-keto esters.通过膦催化的烯酮与β,γ-不饱和α-酮酯的[4+2]环加成反应，高对映选择性合成 3,4-二氢吡喃。
J Am Chem Soc. 2015 Jan 14;137(1):54-7. doi: 10.1021/ja5109358. Epub 2014 Dec 8.
4
A computational study: reactivity difference between phosphine- and amine-catalyzed cycloadditions of allenoates and enones.计算研究：膦和胺催化的丙二烯酸酯和烯酮环加成反应的反应活性差异。
J Org Chem. 2014 Feb 21;79(4):1700-11. doi: 10.1021/jo402609v. Epub 2014 Feb 4.
5
Enantioselective intramolecular formal [2 + 4] annulation of acrylates and α,β-unsaturated imines catalyzed by amino acid derived phosphines.手性氨基酸衍生膦催化的丙烯酸酯和α,β-不饱和亚胺的分子内对映选择性[2 + 4]环加成反应。
Org Lett. 2012 Jun 15;14(12):3226-9. doi: 10.1021/ol3013588. Epub 2012 Jun 7.
6
Origins of the diastereoselectivity in hydrogen bonding directed Diels-Alder reactions of chiral dienes with achiral dienophiles: a computational study.氢键导向的手性二烯与非手性亲二烯体 Diels-Alder 反应中立体选择性的起源：计算研究。
Org Biomol Chem. 2011 Dec 7;9(23):8079-88. doi: 10.1039/c1ob06285a. Epub 2011 Oct 11.
7
Development of a formal catalytic asymmetric [4+2] addition of ethyl-2,3-butadienoate with acyclic enones.发展一种具有非环烯酮的乙基-2,3-丁二烯酸酯的正式催化不对称[4+2]加成。
Org Lett. 2011 Nov 4;13(21):5732-5. doi: 10.1021/ol202301f. Epub 2011 Oct 4.
8
Enantioselective amine-catalyzed [4+2] annulations of allenoates and oxo-dienes: an asymmetric synthesis of dihydropyrans.对映选择性胺催化的联烯酸酯与氧代二烯的[4+2]环化反应：二氢吡喃的不对称合成
Angew Chem Int Ed Engl. 2011 May 27;50(23):5361-4. doi: 10.1002/anie.201100945.
9
The Diels--Alder reaction in total synthesis.狄尔斯-阿尔德反应在全合成中的应用
Angew Chem Int Ed Engl. 2002 May 17;41(10):1668-98. doi: 10.1002/1521-3773(20020517)41:10<1668::aid-anie1668>3.0.co;2-z.
10
Catalytic enantioselective Diels--Alder reactions: methods, mechanistic fundamentals, pathways, and applications.催化对映选择性狄尔斯-阿尔德反应：方法、机理基础、途径及应用
Angew Chem Int Ed Engl. 2002 May 17;41(10):1650-67. doi: 10.1002/1521-3773(20020517)41:10<1650::aid-anie1650>3.0.co;2-b.
Zotero 插件