烯基锡烷对亚甲基米氏酸的不对称加成。
Asymmetric addition of alkenylstannanes to alkylidene Meldrum's acids.
机构信息
Department of Chemistry, University of Waterloo, Waterloo, Ontario N2L 3G1, Canada.
出版信息
Org Lett. 2009 Nov 19;11(22):5346-9. doi: 10.1021/ol902216y.
PMID:19856944
Abstract
Herein, we describe enantioselective addition of alkenyltin reagents possessing a reactive and sensitive allylic functionality not readily available to other classes of alkenyl metals. This method is enabled by the use of highly electrophilic alkylidene Meldrum's acids as acceptors and a cationic Rh(I)-diene complex as catalyst.
摘要
在此，我们描述了具有反应性和敏感性烯丙基官能团的烯基锡试剂的对映选择性加成，而其他烯属金属则不易获得此类官能团。该方法的实现得益于使用高亲电性的亚甲基 Meldrum's 酸作为受体和阳离子 Rh(I)-二烯络合物作为催化剂。
相似文献
1
Asymmetric addition of alkenylstannanes to alkylidene Meldrum's acids.烯基锡烷对亚甲基米氏酸的不对称加成。
Org Lett. 2009 Nov 19;11(22):5346-9. doi: 10.1021/ol902216y.
2
Meldrum's acids and 5-alkylidene Meldrum's acids in catalytic carbon-carbon bond-forming processes.Meldrum 酸和 5-亚甲基 Meldrum 酸在催化碳-碳键形成过程中的应用。
Acc Chem Res. 2010 Mar 16;43(3):440-54. doi: 10.1021/ar900229z.
3
Asymmetric synthesis of all-carbon benzylic quaternary stereocenters via conjugate addition to alkylidene and indenylidene Meldrum's acids.通过共轭加成到亚甲基和茚满基 Meldrum's 酸构建全碳苄基季碳立体中心的不对称合成。
J Org Chem. 2009 Nov 20;74(22):8583-94. doi: 10.1021/jo901559d.
4
Asymmetric synthesis of all-carbon benzylic quaternary stereocenters via Cu-catalyzed conjugate addition of dialkylzinc reagents to 5-(1-arylalkylidene) Meldrum's acids.通过铜催化二烷基锌试剂对5-(1-芳基亚烷基)丙二酸亚异丙酯的共轭加成实现全碳苄基季碳立体中心的不对称合成。
J Am Chem Soc. 2006 Mar 8;128(9):2774-5. doi: 10.1021/ja056692e.
5
Yb(OTf)3-catalyzed reactions of 5-alkylidene Meldrum's acids with phenols: one-pot assembly of 3,4-dihydrocoumarins, 4-chromanones, coumarins, and chromones.Yb(OTf)₃催化5-亚烷基丙二酸亚异丙酯与酚类的反应：3,4-二氢香豆素、4-色满酮、香豆素和色酮的一锅法合成
J Org Chem. 2006 Jan 6;71(1):409-12. doi: 10.1021/jo052000t.
6
Asymmetric conjugate addition reactions of Meldrum's acid derived acceptors employing chiral phosphoramidite ligands.使用手性亚磷酰胺配体的丙二酸亚异丙酯衍生受体的不对称共轭加成反应。
Org Lett. 2003 Nov 27;5(24):4557-8. doi: 10.1021/ol035575q.
7
Practical asymmetric conjugate alkynylation of Meldrum's acid-derived acceptors: access to chiral beta-alkynyl acids.Meldrum's 酸衍生受体的实用不对称共轭炔基化：手性β-炔基酸的获得。
J Am Chem Soc. 2010 Jan 20;132(2):436-7. doi: 10.1021/ja909105s.
8
Sc(OTf)3-catalyzed conjugate allylation of alkylidene Meldrum's acids.
Org Lett. 2009 May 7;11(9):1919-22. doi: 10.1021/ol9003959.
9
Alkylidene Meldrum's Acids as Platforms for the Vinylogous Synthesis of Dihydropyranones.亚甲基 Meldrum's 酸作为合成二氢吡喃酮的乙烯基类似物合成的平台。
Angew Chem Int Ed Engl. 2021 May 10;60(20):11110-11114. doi: 10.1002/anie.202014489. Epub 2021 Apr 6.
10
Probing persistent intramolecular C-H...X (X = O, S, Br, Cl, and F) bonding in solution using benzyl Meldrum's acid derivatives.使用苄基丙二酸亚异丙酯衍生物探究溶液中持久的分子内C-H...X（X = O、S、Br、Cl和F）键
J Org Chem. 2009 Feb 6;74(3):1259-67. doi: 10.1021/jo802311w.
引用本文的文献
1
Enantioselective nickel-catalyzed electrochemical reductive conjugate alkenylation of α,β-unsaturated ketones.镍催化的α,β-不饱和酮的对映选择性电化学还原共轭烯基化反应。
Chem Sci. 2024 Nov 20;16(2):802-808. doi: 10.1039/d4sc06891b. eCollection 2025 Jan 2.
2
Addition of arylstannanes to alkynes giving -alkenylarylstannanes catalysed cooperatively by a rhodium complex and zinc chloride.在铑配合物和氯化锌的协同催化下，芳基锡烷与炔烃加成生成β-烯基芳基锡烷。
Chem Sci. 2018 Aug 17;9(39):7700-7704. doi: 10.1039/c8sc02459f. eCollection 2018 Oct 21.
3
Acyclic quaternary centers from asymmetric conjugate addition of alkylzirconium reagents to linear trisubstituted enones.通过烷基锆试剂与线性三取代烯酮的不对称共轭加成反应构建无环季碳中心。
Chem Sci. 2017 Jan 1;8(1):641-646. doi: 10.1039/c6sc02811j. Epub 2016 Sep 2.
4
Catalytic enantioselective formation of chiral-bridged dienes which are themselves ligands for enantioselective catalysis.手性桥联二烯的催化对映选择性形成，其本身就是对映选择性催化的配体。
Org Lett. 2010 Jan 1;12(1):172-5. doi: 10.1021/ol9025793.
Zotero 插件