烯丙酰胺羟烷化反应：通过钌催化的羰基反氨烯丙基化反应合成 1,2-氨基醇。
Allenamide hydro-hydroxyalkylation: 1,2-amino alcohols via ruthenium-catalyzed carbonyl anti-aminoallylation.
机构信息
University of Texas at Austin, Department of Chemistry and Biochemistry, Austin, Texas 78712, USA.
出版信息
Org Lett. 2010 Jun 4;12(11):2514-6. doi: 10.1021/ol1007235.
Abstract
Exposure of alcohols to allenamides in the presence of RuHCl(CO)(PPh(3))(3) and dippf [dippf = bis(diisopropylphosphino)ferrocene] results in hydrogen transfer to generate aldehyde-allylruthenium pairs, which engage in C-C coupling to form products of carbonyl aminoallylation as single anti-diastereomers.
摘要
醇在 RuHCl(CO)(PPh(3))(3) 和 dippf（二异丙基膦二茂铁）存在下与烯丙酰胺接触会发生氢转移，生成醛-烯丙基钌对，它们进行 C-C 偶联形成羰基氨基烯丙化产物的单非对映异构体。
相似文献
1
Allenamide hydro-hydroxyalkylation: 1,2-amino alcohols via ruthenium-catalyzed carbonyl anti-aminoallylation.烯丙酰胺羟烷化反应：通过钌催化的羰基反氨烯丙基化反应合成 1,2-氨基醇。
Org Lett. 2010 Jun 4;12(11):2514-6. doi: 10.1021/ol1007235.
2
anti-Aminoallylation of aldehydes via ruthenium-catalyzed transfer hydrogenative coupling of sulfonamido allenes: 1,2-aminoalcohols.通过钌催化的磺酰胺基丙二烯转移氢化偶联实现醛的抗氨甲酰化反应：1,2-氨基醇
J Am Chem Soc. 2009 Apr 15;131(14):5054-5. doi: 10.1021/ja900827p.
3
Enantioselective ruthenium-catalyzed carbonyl allylation via alkyne-alcohol C-C bond-forming transfer hydrogenation: allene hydrometalation vs oxidative coupling.通过炔醇碳-碳键形成转移氢化实现对映选择性钌催化的羰基烯丙基化反应：丙二烯氢金属化与氧化偶联
J Am Chem Soc. 2015 Mar 11;137(9):3161-4. doi: 10.1021/jacs.5b00747. Epub 2015 Mar 3.
4
Highly enantioselective synthesis of chiral cyclic amino alcohols and conhydrine by ruthenium-catalyzed asymmetric hydrogenation.钌催化不对称氢化法高对映选择性合成手性环状氨基醇和吐根碱
Org Lett. 2009 Nov 5;11(21):4994-7. doi: 10.1021/ol901605a.
5
syn-1,2-Amino alcohols via diastereoselective allylic C-H amination.通过非对映选择性烯丙基C-H胺化反应合成1,2-氨基醇
J Am Chem Soc. 2007 Jun 13;129(23):7274-6. doi: 10.1021/ja071905g. Epub 2007 May 22.
6
Regioselective Hydrohydroxyalkylation of Styrene with Primary Alcohols or Aldehydes via Ruthenium-Catalyzed C-C Bond Forming Transfer Hydrogenation.通过钌催化的 C-C 键形成转移氢化反应实现苯乙烯与伯醇或醛的区域选择性氢羟烷基化。
Angew Chem Int Ed Engl. 2016 Dec 23;55(52):16119-16122. doi: 10.1002/anie.201609056. Epub 2016 Dec 2.
7
Ruthenium-catalyzed C-C bond forming transfer hydrogenation: carbonyl allylation from the alcohol or aldehyde oxidation level employing acyclic 1,3-dienes as surrogates to preformed allyl metal reagents.钌催化的碳-碳键形成转移氢化反应：以无环1,3-二烯作为预制烯丙基金属试剂的替代物，从醇或醛氧化态进行羰基烯丙基化反应。
J Am Chem Soc. 2008 May 21;130(20):6338-9. doi: 10.1021/ja801213x. Epub 2008 Apr 29.
8
Alkynes as allylmetal equivalents in redox-triggered C-C couplings to primary alcohols: (Z)-homoallylic alcohols via ruthenium-catalyzed propargyl C-H oxidative addition.炔烃作为氧化还原引发的与伯醇进行C-C偶联反应中烯丙基金属等价物：通过钌催化的炔丙基C-H氧化加成反应制备(Z)-高烯丙醇。
J Am Chem Soc. 2014 Aug 27;136(34):11902-5. doi: 10.1021/ja505962w. Epub 2014 Jul 30.
9
Enantioselective Ruthenium-BINAP-Catalyzed Carbonyl Reductive Coupling of Alkoxyallenes: Convergent Construction of -Diols via ()-σ-Allylmetal Intermediates.手性钌-BINAP 催化的烷氧基丙二烯的羰基还原偶联反应：通过 ()-σ-烯丙基金属中间体构建 -二醇的会聚合成。
J Am Chem Soc. 2021 Jun 16;143(23):8849-8854. doi: 10.1021/jacs.1c03480. Epub 2021 Jun 1.
10
Alkyne-aldehyde reductive C-C coupling through ruthenium-catalyzed transfer hydrogenation: direct regio- and stereoselective carbonyl vinylation to form trisubstituted allylic alcohols in the absence of premetallated reagents.通过钌催化转移氢化实现炔醛的还原 C-C 偶联：在不存在预金属化试剂的情况下，通过直接区域和立体选择性羰基乙烯化形成三取代烯丙醇。
Chemistry. 2011 Oct 24;17(44):12437-43. doi: 10.1002/chem.201101554. Epub 2011 Sep 27.
引用本文的文献
1
Catalytic Enantioselective C-C Coupling of Alcohols for Polyketide Total Synthesis beyond Chiral Auxiliaries and Premetalated Reagents.超越手性助剂和预金属化试剂的醇催化对映选择性碳-碳偶联用于聚酮全合成
Chem Rev. 2024 Dec 25;124(24):13715-13735. doi: 10.1021/acs.chemrev.4c00858. Epub 2024 Dec 6.
2
Leveraging the Stereochemical Complexity of Octahedral Diastereomeric-at-Metal Catalysts to Unlock Regio-, Diastereo-, and Enantioselectivity in Alcohol-Mediated C-C Couplings via Hydrogen Transfer.利用八面体金属中心非对映异构催化剂的立体化学复杂性，通过氢转移在醇介导的碳-碳偶联反应中实现区域、非对映和对映选择性。
J Am Chem Soc. 2024 Mar 27;146(12):7905-7914. doi: 10.1021/jacs.4c01857. Epub 2024 Mar 13.
3
Synthesis of 1,2-Aminoalcohols through Enantioselective Aminoallylation of Ketones by Cu-Catalyzed Reductive Coupling.酮的铜催化还原偶联对映选择性氨基烯丙基化合成 1,2-氨基醇。
Org Lett. 2021 Aug 20;23(16):6444-6449. doi: 10.1021/acs.orglett.1c02258. Epub 2021 Aug 4.
4
Allenes and Dienes as Chiral Allylmetal Pronucleophiles in Catalytic Enantioselective C=X Addition: Historical Perspective and State-of-The-Art Survey.烯丙基试剂和二烯作为手性烯丙基金属亲核试剂在催化对映选择性 C=X 加成反应中的应用：历史透视和最新进展综述。
Chemistry. 2021 Sep 15;27(52):13107-13116. doi: 10.1002/chem.202101890. Epub 2021 Jul 29.
5
Access to Chiral Diamine Derivatives through Stereoselective Cu-Catalyzed Reductive Coupling of Imines and Allenamides.通过手性二胺衍生物通过对亚胺和烯丙酰胺的立体选择性 Cu 催化还原偶联获得。
J Org Chem. 2021 Apr 2;86(7):5026-5046. doi: 10.1021/acs.joc.0c02971. Epub 2021 Mar 16.
6
Inversion of Enantioselectivity in Allene Gas versus Allyl Acetate Reductive Aldehyde Allylation Guided by Metal-Centered Stereogenicity: An Experimental and Computational Study.以金属中心手性为导向的丙二烯气体与乙酸烯丙酯还原醛烯丙基化反应中对映选择性的反转：一项实验与计算研究
ACS Catal. 2019 Oct 4;9(10):9158-9163. doi: 10.1021/acscatal.9b03695. Epub 2019 Sep 11.
7
Access to a Catalytically Generated Umpolung Reagent through the Use of Cu-Catalyzed Reductive Coupling of Ketones and Allenes for the Synthesis of Chiral Vicinal Aminoalcohol Synthons.通过铜催化的酮与丙二烯的还原偶联反应获取一种催化生成的极性反转试剂，用于合成手性邻位氨基醇合成子。
Org Lett. 2019 Dec 6;21(23):9753-9758. doi: 10.1021/acs.orglett.9b03937. Epub 2019 Nov 26.
8
Direct Conversion of Primary Alcohols to 1,2-Amino Alcohols: Enantioselective Iridium-Catalyzed Carbonyl Reductive Coupling of Phthalimido-Allene via Hydrogen Auto-Transfer.直接将伯醇转化为 1,2-氨基醇：通过氢自动转移实现邻苯二甲酰亚胺烯丙基的对映选择性铱催化羰基还原偶联。
J Am Chem Soc. 2019 Sep 11;141(36):14136-14141. doi: 10.1021/jacs.9b08715. Epub 2019 Aug 29.
9
Cyclometalated Iridium-PhanePhos Complexes Are Active Catalysts in Enantioselective Allene-Fluoral Reductive Coupling and Related Alcohol-Mediated Carbonyl Additions That Form Acyclic Quaternary Carbon Stereocenters.环金属铱-菲咯啉配合物是手性选择性丙二烯-氟代还原偶联反应和相关醇介导的羰基加成反应的活性催化剂，这些反应形成非环状季碳立体中心。
J Am Chem Soc. 2019 Feb 6;141(5):2087-2096. doi: 10.1021/jacs.8b11868. Epub 2019 Jan 25.
10
Intermolecular Metal-Catalyzed Reductive Coupling of Dienes, Allenes, and Enynes with Carbonyl Compounds and Imines.分子间金属催化的二烯、丙二烯和炔与羰基化合物和亚胺的还原偶联。
Chem Rev. 2018 Jun 27;118(12):6026-6052. doi: 10.1021/acs.chemrev.8b00213. Epub 2018 Jun 13.
本文引用的文献
1
2
Formation of C-C Bonds via Ruthenium Catalyzed Transfer Hydrogenation: Carbonyl Addition from the Alcohol or Aldehyde Oxidation Level.通过钌催化转移氢化形成碳-碳键：来自醇或醛氧化水平的羰基加成
Chem Lett. 2008;37(11):1102-1107. doi: 10.1246/cl.2008.1102.
3
Hydroacylation of 2-Butyne from the Alcohol or Aldehyde Oxidation Level via Ruthenium Catalyzed C-C Bond Forming Transfer Hydrogenation.通过钌催化的碳-碳键形成转移氢化反应，从醇或醛氧化水平对2-丁炔进行氢酰化反应。
Tetrahedron. 2009 Jun 27;65(26):5024-5029. doi: 10.1016/j.tet.2009.03.068.
4
Synthesis of 2-hydroxymethyl ketones by ruthenium hydride-catalyzed cross-coupling reaction of alpha,beta-unsaturated aldehydes with primary alcohols.铑氢化物催化的α,β-不饱和醛与伯醇的交叉偶联反应合成 2-羟甲基酮。
Org Lett. 2010 Jan 1;12(1):1-3. doi: 10.1021/ol902289r.
5
Dehydrogenation as a substrate-activating strategy in homogeneous transition-metal catalysis.脱氢反应作为均相过渡金属催化中一种底物活化策略。
Chem Rev. 2010 Feb 10;110(2):681-703. doi: 10.1021/cr900202j.
6
Hydrogen autotransfer in the N-alkylation of amines and related compounds using alcohols and amines as electrophiles.使用醇类和胺类作为亲电试剂时，胺类及相关化合物N-烷基化反应中的氢自动转移。
Chem Rev. 2010 Mar 10;110(3):1611-41. doi: 10.1021/cr9002159.
7
Unexpected formation of a cyclopentadienylruthenium alkoxycarbonyl complex with a coordinated C=C bond.意外形成具有配位碳碳双键的环戊二烯基钌烷氧羰基配合物。
J Am Chem Soc. 2009 Sep 30;131(38):13622-4. doi: 10.1021/ja905741w.
8
Protecting-group-free synthesis of 3-tert-prenylated oxindoles: contiguous all-carbon quaternary centers via tertiary neopentyl substitution.3-叔戊烯基异吲哚酮的无保护基合成：通过叔新戊基取代形成连续的全碳季碳中心
Org Lett. 2009 Oct 15;11(20):4485-7. doi: 10.1021/ol9018562.
9
All-carbon quaternary centers via ruthenium-catalyzed hydroxymethylation of 2-substituted butadienes mediated by formaldehyde: beyond hydroformylation.通过甲醛介导的钌催化2-取代丁二烯的羟甲基化反应构建全碳季碳中心：超越氢甲酰化反应
J Am Chem Soc. 2009 Aug 5;131(30):10366-7. doi: 10.1021/ja904124b.
10
Concise synthesis of the bryostatin A-ring via consecutive C-C bond forming transfer hydrogenations.通过连续的碳-碳键形成转移氢化反应简洁合成苔藓抑素A环。
Org Lett. 2009 Jul 16;11(14):3108-11. doi: 10.1021/ol901096d.
Zotero 插件