Copper-Catalyzed Asymmetric Carboboronation of Allenes to Access α-Quaternary Amino Esters with Adjacent Stereocenters
Tài liệu tham khảo
Fuji, 1993, Asymmetric Creation of Quaternary Carbon Centers, Chem. Rev., 93, 2037, 10.1021/cr00022a005
Corey, 1998, The Catalytic Enantioselective Construction of Molecules with Quaternary Carbon Stereocenters, Angew. Chem. Int. Ed. Engl., 37, 388, 10.1002/(SICI)1521-3773(19980302)37:4<388::AID-ANIE388>3.0.CO;2-V
Christoffers, 2005, Stereoselective Construction of Quaternary Stereocenters, Adv. Synth. Catal., 347, 1473, 10.1002/adsc.200505165
Trost, 2006, Catalytic Enantioselective Construction of All-Carbon Quaternary Stereocenters, Synthesis, 3, 369, 10.1055/s-2006-926302
Liu, 2015, Catalytic enantioselective construction of quaternary stereocenters: assembly of key building blocks for the synthesis of biologically active molecules, Acc. Chem. Res., 48, 740, 10.1021/ar5004658
Zeng, 2016, Catalytic Enantioselective Desymmetrization Reactions to All-Carbon Quaternary Stereocenters, Chem. Rev., 116, 7330, 10.1021/acs.chemrev.6b00094
Feng, 2017, Acyclic Quaternary Carbon Stereocenters via Enantioselective Transition Metal Catalysis, Chem. Rev., 117, 12564, 10.1021/acs.chemrev.7b00385
Ohfune, 2005, Enantio- and Diastereoselective Construction of α,α-Disubstituted α-Amino Acids for the Synthesis of Biologically Active Compounds, Eur. J. Org. Chem., 2005, 5127, 10.1002/ejoc.200500434
Cativiela, 2007, Recent Progress on the Stereoselective Synthesis of Acyclic Quaternary α-Amino Acids, Tetrahedron Asymmetry, 18, 569, 10.1016/j.tetasy.2007.02.003
Najera, 2007, Catalytic asymmetric synthesis of α-amino acids, Chem. Rev., 107, 4584, 10.1021/cr050580o
Vogt, 2007, Recent approaches towards the asymmetric synthesis of α,α-disubstituted α-amino acids, Org. Biomol. Chem., 5, 406, 10.1039/B611091F
Cativiela, 2009, Recent Progress on the Stereoselective Synthesis of Cyclic Quaternary α-Amino Acids, Tetrahedron Asymmetry, 20, 1, 10.1016/j.tetasy.2009.01.002
Hughes, 2011
Pollegioni, 2012
Trost, 2001, gem-Diacetates as carbonyl surrogates for asymmetric synthesis. Total syntheses of sphingofungins E and F, J. Am. Chem. Soc., 123, 12191, 10.1021/ja0118338
Kende, 1995, Total Synthesis of (-)-Altemicidin—A Novel Exploitation of the Potier-Polonovski Rearrangement, J. Am. Chem. Soc., 117, 10597, 10.1021/ja00147a032
Hu, 2019, Aminoacyl sulfonamide assembly in SB-203208 biosynthesis, Nat. Commun., 10, 184, 10.1038/s41467-018-08093-x
Corey, 1992, Total Synthesis of Lactacystin, J. Am. Chem. Soc., 114, 10677, 10.1021/ja00052a096
Fenteany, 1995, Inhibition of proteasome activities and subunit-specific amino-terminal threonine modification by lactacystin, Science, 268, 726, 10.1126/science.7732382
Huo, 2017, Stereoselective and Site-Specific Allylic Alkylation of Amino Acids and Small Peptides via a Pd/Cu Dual Catalysis, J. Am. Chem. Soc., 139, 9819, 10.1021/jacs.7b05460
Huo, 2018, Ir/Cu Dual Catalysis: Enantio- and Diastereodivergent Access to α,α-Disubstituted α-Amino Acids Bearing Vicinal Stereocenters, J. Am. Chem. Soc., 140, 2080, 10.1021/jacs.8b00187
Wei, 2017, Synergistic Cu/Pd Catalysis for Enantioselective Allylic Alkylation of Aldimine Esters: Access to α,α-Disubstituted α-Amino Acids, Angew. Chem. Int. Ed. Engl., 56, 12312, 10.1002/anie.201707019
Wei, 2018, Stereodivergent Synthesis of α,α-Disubstituted α-Amino Acids via Synergistic Cu/Ir Catalysis, J. Am. Chem. Soc., 140, 1508, 10.1021/jacs.7b12174
Wei, 2019, Synergistic catalysis for cascade allylation and 2-aza-cope rearrangement of azomethine ylides, Nat. Commun., 10, 1594, 10.1038/s41467-019-09563-6
Zhang, 2019, Stereodivergent Coupling of 1,3-Dienes with Aldimine Esters Enabled by Synergistic Pd and Cu Catalysis, J. Am. Chem. Soc., 141, 14554, 10.1021/jacs.9b07600
Ramón, 2005, Asymmetric multicomponent reactions (AMCRs): the new frontier, Angew. Chem. Int. Ed. Engl., 44, 1602, 10.1002/anie.200460548
Enders, 2007, Asymmetric organocatalytic domino reactions, Angew. Chem. Int. Ed. Engl., 46, 1570, 10.1002/anie.200603129
Jeganmohan, 2008, Transition metal-catalyzed three-component coupling of allenes and the related allylation reactions, Chem. Commun. (Camb.), 3101, 10.1039/b800440d
Touré, 2009, Natural product synthesis using multicomponent reaction strategies, Chem. Rev., 109, 4439, 10.1021/cr800296p
Yu, 2011, Brønsted-acid-catalyzed asymmetric multicomponent reactions for the facile synthesis of highly enantioenriched structurally diverse nitrogenous heterocycles, Acc. Chem. Res., 44, 1156, 10.1021/ar2000343
de Graaff, 2012, Recent developments in asymmetric multicomponent reactions, Chem. Soc. Rev., 41, 3969, 10.1039/c2cs15361k
Cioc, 2014, Multicomponent Reactions: Advanced Tools for Sustainable Organic Synthesis, Green Chem., 16, 2958, 10.1039/C4GC00013G
Tsuji, 2016, Copper-Catalyzed Transformations Using Cu-H, Cu-B, and Cu-Si as Active Catalyst Species, Chem. Rec., 16, 2294, 10.1002/tcr.201600039
Pulis, 2017, Enantioselective copper catalysed, direct functionalisation of allenes via allyl copper intermediates, Chem. Sci. (Camb.), 8, 5240, 10.1039/C7SC01968H
Sieber, 2006, Sequential Pd-catalyzed asymmetric allene diboration/α-aminoallylation, J. Am. Chem. Soc., 128, 74, 10.1021/ja057020r
Jiang, 2016, Highly Diastereo- and Enantioselective Cu-Catalyzed Borylative Coupling of 1,3-Dienes and Aldimines, Angew. Chem. Int. Ed. Engl., 55, 13854, 10.1002/anie.201607493
Rae, 2016, Copper-Catalyzed Borylative Cross-Coupling of Allenes and Imines: Selective Three-Component Assembly of Branched Homoallyl Amines, Angew. Chem. Int. Ed. Engl., 55, 1102, 10.1002/anie.201508959
Yeung, 2016, Enantioselective Generation of Adjacent Stereocenters in a Copper-Catalyzed Three-Component Coupling of Imines, Allenes, and Diboranes, Angew. Chem. Int. Ed. Engl., 55, 11912, 10.1002/anie.201606710
Jang, 2017, Catalytic diastereo- and enantioselective additions of versatile allyl groups to N-H ketimines, Nat. Chem., 9, 1269, 10.1038/nchem.2816
Itoh, 2018, Copper(I)-Catalyzed Enantio- and Diastereodivergent Borylative Coupling of Styrenes and Imines, Angew. Chem. Int. Ed. Engl., 57, 8265, 10.1002/anie.201804117
Deng, 2019, Enantioselective Copper-Catalyzed Three-Component Carboboronation of Allenes: Access to Functionalized Dibenzo [ b,f ][1,4]Oxazepine Derivatives, Adv. Synth. Catal., 361, 3582, 10.1002/adsc.201900503
Zhang, 2019, Delayed catalyst function enables direct enantioselective conversion of nitriles to NH2-amines, Science, 364, 45, 10.1126/science.aaw4029
Yang, 2000, Highly Regio- and Stereoselective Acylboration of Allenes Catalyzed by Palladium Complexes: An Efficient Route to a New Class of 2-Acylallylboronates, J. Am. Chem. Soc., 122, 7122, 10.1021/ja001082u
Yang, 2003, Highly regio- and stereoselective acylboration, acylsilation, and acylstannation of allenes catalyzed by phosphine-free palladium complexes: an efficient route to a new class of 2-acylallylmetal reagents, J. Am. Chem. Soc., 125, 12576, 10.1021/ja036021l
Meng, 2013, Cu-catalyzed chemoselective preparation of 2-(pinacolato)boron-substituted allylcopper complexes and their in situ site-, diastereo-, and enantioselective additions to aldehydes and ketones, Angew. Chem. Int. Ed. Engl., 52, 5046, 10.1002/anie.201301018
Meng, 2014, Diastereo- and enantioselective reactions of bis(pinacolato)diboron, 1,3-enynes, and aldehydes catalyzed by an easily accessible bisphosphine-Cu complex, J. Am. Chem. Soc., 136, 11304, 10.1021/ja5071202
Boreux, 2017, Acyl Fluorides as Efficient Electrophiles for the Copper-Catalyzed Boroacylation of Allenes, ACS Catal., 7, 8200, 10.1021/acscatal.7b02938
Fujihara, 2017, Boraformylation and Silaformylation of Allenes, Angew. Chem. Int. Ed. Engl., 56, 1539, 10.1002/anie.201611314
Chen, 2019, Stereoselective Syntheses of γ-Boryl Substituted syn-β-Alkoxy- and syn-β-Amino-homoallylic Alcohols via a Regio- and Stereoselective Allene Diboration and Aldehyde Allylboration Reaction Sequence, Org. Lett., 21, 4638, 10.1021/acs.orglett.9b01535
Han, 2019, Design and Synthesis of WJ-Phos, and Application in Cu-Catalyzed Enantioselective Boroacylation of 1,1-Disubstituted Allenes, ACS Catal., 9, 6890, 10.1021/acscatal.9b02080
Meng, 2014, Multifunctional organoboron compounds for scalable natural product synthesis, Nature, 513, 367, 10.1038/nature13735
Semba, 2014, Copper-catalyzed borylative allyl-allyl coupling reaction, Angew. Chem. Int. Ed. Engl., 53, 9007, 10.1002/anie.201404173
Yang, 2014, Copper-catalyzed regioselective ortho C-H cyanation of vinylarenes, Angew. Chem. Int. Ed. Engl., 53, 8677, 10.1002/anie.201402449
Meng, 2016, Catalytic enantioselective 1,6-conjugate additions of propargyl and allyl groups, Nature, 537, 387, 10.1038/nature19063
Zhao, 2016, Cascade Copper-Catalyzed 1,2,3-Trifunctionalization of Terminal Allenes, J. Am. Chem. Soc., 138, 9763, 10.1021/jacs.6b05216
Ozawa, 2018, Copper(i)-catalysed regio- and diastereoselective intramolecular alkylboration of terminal allenes via allylcopper(i) isomerization, Chem. Commun. (Camb.), 54, 4991, 10.1039/C8CC02692K
Huang, 2019, Racemic Vinylallenes in Catalytic Enantioselective Multicomponent Processes: Rapid Generation of Complexity through 1,6-Conjugate Additions, Angew. Chem. Int. Ed. Engl., 58, 2685, 10.1002/anie.201812535
Jia, 2019, Enantioselective and Regioselective Copper-Catalyzed Borocyanation of 1-Aryl-1,3-Butadienes, ACS Catal., 9, 6744, 10.1021/acscatal.9b01911
Yeung, 2019, Copper-Catalyzed Borylative Multicomponent Synthesis of Quaternary α-Amino Esters, ACS Catal., 9, 1655, 10.1021/acscatal.8b04563
Spahn, 2013, Double-asymmetric hydrogenation strategy for the reduction of 1,1-diaryl olefins applied to an improved synthesis of CuIPhEt, a C2-symmetric N-heterocyclic carbenoid, J. Org. Chem., 78, 2731, 10.1021/jo3026548
Cai, 2018, Copper-Catalyzed Enantioselective Markovnikov Protoboration of α-Olefins Enabled by a Buttressed N-Heterocyclic Carbene Ligand, Angew. Chem. Int. Ed. Engl., 57, 1376, 10.1002/anie.201711229
Diesel, 2018, Nickel-Catalyzed Enantioselective Pyridone C-H Functionalizations Enabled by a Bulky N-Heterocyclic Carbene Ligand, J. Am. Chem. Soc., 140, 4489, 10.1021/jacs.8b01181
Cai, 2019, Nickel/NHC-Catalyzed Asymmetric C-H Alkylation of Fluoroarenes with Alkenes: Synthesis of Enantioenriched Fluorotetralins, Angew. Chem. Int. Ed. Engl., 58, 13433, 10.1002/anie.201907387
Cai, 2019, Nickel/N-Heterocyclic Carbene Complex-Catalyzed Enantioselective Redox-Neutral Coupling of Benzyl Alcohols and Alkynes to Allylic Alcohols, ACS Catal., 9, 1, 10.1021/acscatal.8b04198
Diesel, 2019, A Bulky Chiral N-Heterocyclic Carbene Nickel Catalyst Enables Enantioselective C-H Functionalizations of Indoles and Pyrroles, Angew. Chem. Int. Ed. Engl., 58, 11044, 10.1002/anie.201904774
Shen, 2019, A Bulky Chiral N-Heterocyclic Carbene Palladium Catalyst Enables Highly Enantioselective Suzuki-Miyaura Cross-Coupling Reactions for the Synthesis of Biaryl Atropisomers, J. Am. Chem. Soc., 141, 14938, 10.1021/jacs.9b08578
Zhang, 2019, Regio- and Enantioselective C-H Cyclization of Pyridines with Alkenes Enabled by a Nickel/N-Heterocyclic Carbene Catalysis, J. Am. Chem. Soc., 141, 5628, 10.1021/jacs.9b00931
Matsunaga, 2005, Synthetic Utility of Five-Membered Heterocycles: Chiral Functionalization and Applications, Tetrahedron, 61, 8073, 10.1016/j.tet.2005.05.076
Baumann, 2011, An overview of the key routes to the best selling 5-membered ring heterocyclic pharmaceuticals, Beilstein J. Org. Chem., 7, 442, 10.3762/bjoc.7.57