铜催化的不对称共轭还原反应：一种合成新型β-氮杂环酸衍生物的途径。
Copper-catalyzed asymmetric conjugate reduction as a route to novel beta-azaheterocyclic acid derivatives.
作者信息
Rainka Matthew P, Aye Yimon, Buchwald Stephen L
机构信息
Department of Chemistry, Massachusetts Institute of Technology, Cambridge, MA 02139, USA.
出版信息
Proc Natl Acad Sci U S A. 2004 Apr 20;101(16):5821-3. doi: 10.1073/pnas.0307764101. Epub 2004 Apr 5.
Abstract
A chiral copper-hydride catalyst for the asymmetric conjugate reduction of alpha,beta-unsaturated carbonyl compounds has been used for the reduction of substrates containing beta-nitrogen substituents. A new set of reaction conditions has allowed for a variety of beta-azaheterocyclic acid derivatives to be synthesized in excellent yields and with high degrees of enantioselectivity. In addition, the effect that the nature of the nitrogen substituent has on the rate of the conjugate reduction reaction has been explored.
摘要
一种用于α,β-不饱和羰基化合物不对称共轭还原的手性氢化铜催化剂已被用于还原含有β-氮取代基的底物。一组新的反应条件使得多种β-氮杂环酸衍生物得以以优异的产率和高度的对映选择性合成。此外，还探索了氮取代基的性质对共轭还原反应速率的影响。
相似文献
1
Copper-catalyzed asymmetric conjugate reduction as a route to novel beta-azaheterocyclic acid derivatives.铜催化的不对称共轭还原反应：一种合成新型β-氮杂环酸衍生物的途径。
Proc Natl Acad Sci U S A. 2004 Apr 20;101(16):5821-3. doi: 10.1073/pnas.0307764101. Epub 2004 Apr 5.
2
Heterogeneous versus homogeneous copper(II) catalysis in enantioselective conjugate-addition reactions of boron in water.水相中硼的对映选择性共轭加成反应中的非均相铜（II）催化与均相铜（II）催化
Chem Asian J. 2014 Jan;9(1):179-88. doi: 10.1002/asia.201300997. Epub 2013 Sep 20.
3
Rapid Synthesis of Chiral 1,2-Bisphosphine Derivatives through Copper(I)-Catalyzed Asymmetric Conjugate Hydrophosphination.通过铜（I）催化的不对称共轭氢膦化反应快速合成手性 1,2-双膦衍生物。
Angew Chem Int Ed Engl. 2020 Apr 27;59(18):7057-7062. doi: 10.1002/anie.201916076. Epub 2020 Mar 11.
4
Synthesis and application of a dual chiral [2.2]paracyclophane-based N-heterocyclic carbene in enantioselective β-boration of acyclic enones.基于双手性[2.2]对环芳烷的 N-杂环卡宾的合成及其在手性β-硼化非环烯酮中的应用。
Org Biomol Chem. 2015 Nov 21;13(43):10691-8. doi: 10.1039/c5ob01609f.
5
Highly enantioselective Cu(I)-Tol-BINAP-catalyzed asymmetric conjugate addition of Grignard reagents to α,β-unsaturated esters.高对映选择性的 Cu(I)-Tol-BINAP 催化的格氏试剂对α,β-不饱和酯的不对称共轭加成。
Chem Commun (Camb). 2010 Dec 14;46(46):8694-703. doi: 10.1039/c0cc03211e. Epub 2010 Oct 29.
6
Copper-catalyzed asymmetric hydroboration of α-dehydroamino acid derivatives: facile synthesis of chiral β-hydroxy-α-amino acids.铜催化的α-去氢氨基酸衍生物的不对称硼氢化反应：手性β-羟基-α-氨基酸的简便合成。
Org Lett. 2014 Mar 7;16(5):1426-9. doi: 10.1021/ol500219e. Epub 2014 Feb 14.
7
Enantioselective synthesis of beta-aryl-gamma-amino acid derivatives via Cu-catalyzed asymmetric 1,4-reductions of gamma-phthalimido-substituted alpha,beta-unsaturated carboxylic acid esters.通过铜催化的γ-邻苯二甲酰亚胺取代的α,β-不饱和羧酸酯的不对称1,4-还原反应对β-芳基-γ-氨基酸衍生物进行对映选择性合成。
J Org Chem. 2008 Aug 1;73(15):6022-4. doi: 10.1021/jo800794p. Epub 2008 Jul 3.
8
Copper-catalyzed enantioselective Henry reaction of enals and subsequent iodocyclization: stereoselective construction of chiral azatricyclic frameworks.铜催化烯醛的对映选择性亨利反应及后续碘环化反应：手性氮杂三环骨架的立体选择性构建
Angew Chem Int Ed Engl. 2013 Sep 23;52(39):10265-9. doi: 10.1002/anie.201305148. Epub 2013 Aug 9.
9
Amino acids as the nitrogen-containing motifs in copper-catalyzed domino synthesis of N-heterocycles.氨基酸作为含氮基团在铜催化的 N-杂环稠合反应中的应用。
J Org Chem. 2011 May 20;76(10):3846-52. doi: 10.1021/jo2002227. Epub 2011 Apr 6.
10
Copper(I)-Catalyzed Asymmetric Conjugate 1,6-, 1,8-, and 1,10-Borylation.铜（I）催化的不对称共轭 1,6-、1,8-和 1,10-硼化反应。
Angew Chem Int Ed Engl. 2021 Apr 19;60(17):9493-9499. doi: 10.1002/anie.202016081. Epub 2021 Mar 18.
引用本文的文献
1
Enantioselective synthesis of N-alkylindoles enabled by nickel-catalyzed C-C coupling.镍催化 C-C 偶联实现 N-烷基吲哚的对映选择性合成。
Nat Commun. 2022 Nov 11;13(1):6861. doi: 10.1038/s41467-022-34615-9.
2
Synthesis of -aryl β-amino acid derivatives Cu(ii)-catalyzed asymmetric 1,4-reduction in air.-芳基β-氨基酸衍生物的合成：空气中铜（II）催化的不对称1,4-还原反应。
RSC Adv. 2019 Mar 20;9(16):9187-9192. doi: 10.1039/c9ra01203f. eCollection 2019 Mar 15.
3
CuH-Catalyzed Olefin Functionalization: From Hydroamination to Carbonyl Addition.CuH 催化的烯烃官能化：从氨氢化反应到羰基加成反应。
Acc Chem Res. 2020 Jun 16;53(6):1229-1243. doi: 10.1021/acs.accounts.0c00164. Epub 2020 May 13.
4
Catalytic Reductive Aldol and Mannich Reactions of Enone, Acrylate, and Vinyl Heteroaromatic Pronucleophiles.烯酮、丙烯酸盐和乙烯基杂芳烃给电子体的催化还原Aldol 和 Mannich 反应。
Chem Rev. 2020 Apr 22;120(8):3721-3748. doi: 10.1021/acs.chemrev.0c00053. Epub 2020 Mar 19.
5
The inverted ketene synthon: a double umpolung approach to enantioselective β-amino amide synthesis.内酮烯合成子：一种用于对映选择性β-氨基酰胺合成的双重极性翻转方法。
Chem Sci. 2018 Nov 12;10(4):1138-1143. doi: 10.1039/c8sc04330b. eCollection 2019 Jan 28.
6
Copper-Catalyzed Enantioselective Addition of Styrene-Derived Nucleophiles to Imines Enabled by Ligand-Controlled Chemoselective Hydrocupration.铜催化的苯乙烯衍生亲核试剂对亚胺的对映选择性加成反应通过配体控制的化学选择性氢铜化实现。
J Am Chem Soc. 2016 Aug 10;138(31):9787-90. doi: 10.1021/jacs.6b06299. Epub 2016 Aug 1.
7
Copper Hydride Catalyzed Hydroamination of Alkenes and Alkynes.氢化铜催化的烯烃和炔烃的氢胺化反应
Angew Chem Int Ed Engl. 2016 Jan 4;55(1):48-57. doi: 10.1002/anie.201507594. Epub 2015 Dec 10.
8
Design of Modified Amine Transfer Reagents Allows the Synthesis of α-Chiral Secondary Amines via CuH-Catalyzed Hydroamination.改性胺转移试剂的设计使得通过CuH催化的氢胺化反应合成α-手性仲胺成为可能。
J Am Chem Soc. 2015 Aug 5;137(30):9716-21. doi: 10.1021/jacs.5b05446. Epub 2015 Jul 21.
9
Highly diastereo- and enantioselective CuH-catalyzed synthesis of 2,3-disubstituted indolines.铜氢催化的2,3-二取代二氢吲哚的高非对映选择性和对映选择性合成。
J Am Chem Soc. 2015 Apr 15;137(14):4666-9. doi: 10.1021/jacs.5b02316. Epub 2015 Apr 6.
10
Copper-catalysed selective hydroamination reactions of alkynes.铜催化炔烃的选择性氨氢化反应。
Nat Chem. 2015 Jan;7(1):38-44. doi: 10.1038/nchem.2131. Epub 2014 Dec 15.
本文引用的文献
1
Catalytic enantioselective synthesis of beta3-amino acids.β3-氨基酸的催化对映选择性合成
Angew Chem Int Ed Engl. 2002 Jun 17;41(12):2197-9.
2
Catalytic enantioselective conjugate reduction of lactones and lactams.内酯和内酰胺的催化对映选择性共轭还原
J Am Chem Soc. 2003 Sep 17;125(37):11253-8. doi: 10.1021/ja0351692.
3
Catalytic enantioselective conjugate reduction of beta,beta-disubstituted nitroalkenes.β,β-二取代硝基烯烃的催化对映选择性共轭还原反应。
Angew Chem Int Ed Engl. 2003 Oct 13;42(39):4793-5. doi: 10.1002/anie.200352175.
4
CuH-catalyzed asymmetric conjugate reductions of acyclic enones.铜氢催化的非环状烯酮的不对称共轭还原反应。
Angew Chem Int Ed Engl. 2003 Oct 13;42(39):4789-92. doi: 10.1002/anie.200352313.
5
Copper-catalyzed coupling of amides and carbamates with vinyl halides.铜催化酰胺和氨基甲酸酯与卤代乙烯的偶联反应。
Org Lett. 2003 Oct 2;5(20):3667-9. doi: 10.1021/ol035355c.
6
Recent developments in the catalytic asymmetric synthesis of alpha- and beta-amino acids.α-氨基酸和β-氨基酸催化不对称合成的最新进展。
Angew Chem Int Ed Engl. 2003 Sep 22;42(36):4290-9. doi: 10.1002/anie.200301600.
7
Tweaking copper hydride (CuH) for synthetic gain. A practical, one-pot conversion of dialkyl ketones to reduced trialkylsilyl ether derivatives.
Org Lett. 2003 Aug 21;5(17):3085-8. doi: 10.1021/ol035164+.
8
Conjugate reduction of alpha,beta-unsaturated carbonyl compounds catalyzed by a copper carbene complex.卡宾铜配合物催化的α,β-不饱和羰基化合物的共轭还原反应。
Org Lett. 2003 Jul 10;5(14):2417-20. doi: 10.1021/ol034560p.
9
Highly enantioselective, catalytic conjugate addition of cyanide to alpha,beta-unsaturated imides.氰化物对α,β-不饱和酰亚胺的高度对映选择性催化共轭加成反应。
J Am Chem Soc. 2003 Apr 16;125(15):4442-3. doi: 10.1021/ja034635k.
10
Asymmetric catalytic Mannich reactions catalyzed by urea derivatives: enantioselective synthesis of beta-aryl-beta-amino acids.脲衍生物催化的不对称催化曼尼希反应：β-芳基-β-氨基酸的对映选择性合成
J Am Chem Soc. 2002 Nov 6;124(44):12964-5. doi: 10.1021/ja028353g.
Zotero 插件