Chiral Squaramide‐Catalyzed Asymmetric Mannich Reactions for Synthesis of Fluorinated 3,3′‐Bisoxindoles
A squaramide‐catalyzed asymmetric Mannich reaction of 3‐fluorooxindoles to isatin‐derived imines for synthesis of fluorinated 3,3′‐bisoxindoles with two contiguous stereocenters under mild conditions was developed. The corresponding 3,3′‐bisoxindoles were obtained in excellent yields with excellent...
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| Published in | Advanced synthesis & catalysis Vol. 360; no. 16; pp. 3164 - 3170 |
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| Main Authors | , |
| Format | Journal Article |
| Language | English |
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Wiley
17.08.2018
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| Abstract | A squaramide‐catalyzed asymmetric Mannich reaction of 3‐fluorooxindoles to isatin‐derived imines for synthesis of fluorinated 3,3′‐bisoxindoles with two contiguous stereocenters under mild conditions was developed. The corresponding 3,3′‐bisoxindoles were obtained in excellent yields with excellent diastereo‐ and enantioselectivities (up to 99% yield, >99:1 dr and >99% ee). What's more, this reaction can be gram‐scaled without compromising yield and stereoselectivity. |
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| AbstractList | A squaramide‐catalyzed asymmetric Mannich reaction of 3‐fluorooxindoles to isatin‐derived imines for synthesis of fluorinated 3,3′‐bisoxindoles with two contiguous stereocenters under mild conditions was developed. The corresponding 3,3′‐bisoxindoles were obtained in excellent yields with excellent diastereo‐ and enantioselectivities (up to 99% yield, >99:1 dr and >99% ee). What's more, this reaction can be gram‐scaled without compromising yield and stereoselectivity. A squaramide‐catalyzed asymmetric Mannich reaction of 3‐fluorooxindoles to isatin‐derived imines for synthesis of fluorinated 3,3′‐bisoxindoles with two contiguous stereocenters under mild conditions was developed. The corresponding 3,3′‐bisoxindoles were obtained in excellent yields with excellent diastereo‐ and enantioselectivities (up to 99% yield, >99:1 dr and >99% ee ). What's more, this reaction can be gram‐scaled without compromising yield and stereoselectivity. magnified image A squaramide-catalyzed asymmetric Mannich reaction of 3-fluorooxindoles to isatin-derived imines for synthesis of fluorinated 3,3-bisoxindoles with two contiguous stereocenters under mild conditions was developed. The corresponding 3,3-bisoxindoles were obtained in excellent yields with excellent diastereo- and enantioselectivities (up to 99% yield, >99:1dr and >99% ee). What's more, this reaction can be gram-scaled without compromising yield and stereoselectivity. |
| Author | Li, Bing‐Yu Du, Da‐Ming |
| Author_xml | – sequence: 1 givenname: Bing‐Yu surname: Li fullname: Li, Bing‐Yu organization: Beijing Institute of Technology – sequence: 2 givenname: Da‐Ming surname: Du fullname: Du, Da‐Ming email: dudm@bit.edu.cn organization: Beijing Institute of Technology |
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| Cites_doi | 10.1039/C5CC03289J 10.1002/cmdc.200700059 10.1002/anie.201608752 10.1021/acs.orglett.7b03713 10.1021/acs.orglett.6b01367 10.1021/jo502270a 10.1016/j.jfluchem.2009.09.015 10.1002/(SICI)1521-3773(19980619)37:11<1496::AID-ANIE1496>3.0.CO;2-U 10.1002/adsc.201700361 10.1021/acs.orglett.5b02160 10.1039/C6RA27710A 10.1021/acs.orglett.7b02628 10.1080/14756360701425014 10.1002/adsc.201700011 10.1021/jm800219f 10.1039/B711844A 10.1002/adsc.201700353 10.1021/acs.orglett.7b02044 10.1021/acs.joc.5b02238 10.1002/anie.201704086 10.1002/adsc.201400581 10.1021/acs.orglett.6b01516 10.1021/jo302048v 10.1002/anie.201704922 10.1002/bkcs.10263 10.1002/ejoc.201500787 10.1021/cr500277b 10.1038/86546 10.1002/anie.201509719 10.1002/adsc.201701198 10.1016/j.jfluchem.2006.05.006 10.1039/B610213C 10.1002/adsc.201300373 10.4155/fmc.09.70 10.1039/C5CC02256H 10.1039/c3ob41267a 10.1016/B978-0-08-095167-6.00106-3 10.1021/acs.joc.7b03084 10.1039/c6ra27710a 10.1039/b610213c 10.1039/c5cc03289j 10.4155/FMC.09.70 10.1039/c5cc02256h 10.1039/b711844a |
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| Keywords | 3,3-DISUBSTITUTED OXINDOLES VINYL SULFONE ACIDS REACTIVITY 3-HALOOXINDOLES Asymmetric catalysis Organocatalysis MEDICINAL CHEMISTRY 3-FLUOROOXINDOLES EFFICIENT ACCESS Mannich addition ENANTIOSELECTIVE CONJUGATE ADDITION CONSTRUCTION Squaramides Bisoxindoles |
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| References | 2017; 7 2015; 36 2015; 17 2018; 360 2015; 51 2008; 37 2015; 80 2018; 83 2016; 18 1998; 110 2008; 51 2012; 77 2018; 20 2014; 356 2017; 359 2016; 55 2001; 7 2013; 11 2015; 115 2017; 56 2010; 131 2013; 355 2017; 19 2015 2007; 2 2012; 25 2006; 127 2007; 22 2009; 1 e_1_2_6_31_2 e_1_2_6_30_2 e_1_2_6_18_2 e_1_2_6_19_2 e_1_2_6_12_2 e_1_2_6_35_2 e_1_2_6_13_2 e_1_2_6_14_1 e_1_2_6_10_2 e_1_2_6_11_1 e_1_2_6_33_2 e_1_2_6_34_1 e_1_2_6_32_2 e_1_2_6_16_2 e_1_2_6_39_2 e_1_2_6_17_2 e_1_2_6_38_2 e_1_2_6_37_2 e_1_2_6_15_2 e_1_2_6_36_2 e_1_2_6_42_1 e_1_2_6_20_2 e_1_2_6_40_2 e_1_2_6_41_1 e_1_2_6_8_2 e_1_2_6_7_2 e_1_2_6_9_2 e_1_2_6_29_2 e_1_2_6_4_2 e_1_2_6_5_1 e_1_2_6_3_2 e_1_2_6_6_2 e_1_2_6_24_2 e_1_2_6_47_2 e_1_2_6_48_1 e_1_2_6_23_2 e_1_2_6_49_1 e_1_2_6_22_2 e_1_2_6_2_1 e_1_2_6_21_2 e_1_2_6_43_2 e_1_2_6_27_2 e_1_2_6_28_1 e_1_2_6_44_2 e_1_2_6_45_1 e_1_2_6_26_2 e_1_2_6_25_2 e_1_2_6_46_2 Mei, HB (WOS:000362749100001) 2015; 2015 Kukhar, VP (WOS:000276093600008) 2009; 1 Hagmann, WK (WOS:000258289800001) 2008; 51 Zhang, BX (WOS:000403017000025) 2017; 56 Tredwell, M. (000441874400024.28) 2012; 25 Xie, C (WOS:000354791400018) 2015; 51 Xie, C (WOS:000393754100016) 2017; 7 Chen, XY (WOS:000408941200020) 2017; 359 Murphy, GK (WOS:000342906100004) 2014; 356 Kim, YS (WOS:000354133600033) 2015; 36 Trost, BM (WOS:000368069200060) 2016; 55 Schlosser, Manfred (MEDLINE:29710919) 1998; 37 Liu, XH (WOS:000366877900077) 2015; 80 Wang, KZ (WOS:000408285600050) 2017; 19 Zuo, J (WOS:000347506400065) 2015; 80 Dalpozzo, R (WOS:000402839300001) 2017; 359 Moskowitz, M (WOS:000424729400065) 2018; 83 Dou, XW (WOS:000322944900003) 2013; 11 Balaraman, K (WOS:000394997700039) 2017; 56 Jang, YJ (WOS:000410810600046) 2017; 56 Paladhi, S (WOS:000412789600084) 2017; 19 Begue, JP (WOS:000239874500001) 2006; 127 Morgenthaler, M (WOS:000248851900001) 2007; 2 Wang, TL (WOS:000356021300025) 2015; 51 Shan, P. (000441874400024.26) 2007; 22 Xie, C (WOS:000379455300058) 2016; 18 Gribkoff, VK (WOS:000167960500043) 2001; 7 Purser, S (WOS:000252411800007) 2008; 37 Yang, XY (WOS:000348689400009) 2015; 115 Zuo, J (WOS:000312564900034) 2012; 77 Li, YX (WOS:000426013600007) 2018; 20 Kaur, J (WOS:000401528100017) 2017; 359 Jiang, XJ (WOS:000379455300029) 2016; 18 Sorochinsky, AE (WOS:000275138300003) 2010; 131 Jing, CC (WOS:000361087200054) 2015; 17 O'Hagan, D (WOS:000252411800006) 2008; 37 Huang, JZ (WOS:000327862400009) 2013; 355 Park, DY (WOS:000424093900013) 2018; 360 |
| References_xml | – volume: 55 start-page: 781 year: 2016 end-page: 784 publication-title: Angew. Chem. Int. Ed. – volume: 20 start-page: 921 year: 2018 end-page: 924 publication-title: Org. Lett. – volume: 11 start-page: 5217 year: 2013 end-page: 5221 publication-title: Org. Biomol. Chem. – volume: 80 start-page: 634 year: 2015 end-page: 640 publication-title: J. Org. Chem. – volume: 7 start-page: 471 year: 2001 end-page: 477 publication-title: Nat. Med. – volume: 7 start-page: 5679 year: 2017 end-page: 5683 publication-title: RSC Adv. – volume: 2 start-page: 1100 year: 2007 end-page: 1115 publication-title: ChemMedChem. – volume: 19 start-page: 5336 year: 2017 end-page: 5339 publication-title: Org. Lett. – volume: 19 start-page: 4351 year: 2017 end-page: 4354 publication-title: Org. Lett. – volume: 359 start-page: 1772 year: 2017 end-page: 1810 publication-title: Adv. Synth. Catal. – volume: 360 start-page: 462 year: 2018 end-page: 467 publication-title: Adv. Synth. Catal. – volume: 36 start-page: 1512 year: 2015 end-page: 1515 publication-title: Bull. Korean Chem. Soc. – volume: 37 start-page: 308 year: 2008 end-page: 319 publication-title: Chem. Soc. Rev. – volume: 56 start-page: 11927 year: 2017 end-page: 11930 publication-title: Angew. Chem. Int. Ed. – volume: 131 start-page: 127 year: 2010 end-page: 139 publication-title: J. Fluorine Chem. – volume: 355 start-page: 2531 year: 2013 end-page: 2537 publication-title: Adv. Synth. Catal. – volume: 80 start-page: 12651 year: 2015 end-page: 12658 publication-title: J. Org. Chem. – volume: 51 start-page: 10186 year: 2015 end-page: 10189 publication-title: Chem. Commun. – volume: 22 start-page: 527 year: 2007 end-page: 540 publication-title: J. Enzyme Inhib. Med. Chem. – volume: 356 start-page: 2919 year: 2014 end-page: 2923 publication-title: Adv. Synth. Catal. – volume: 1 start-page: 793 year: 2009 end-page: 819 publication-title: Future Med. Chem. – volume: 359 start-page: 3057 year: 2017 end-page: 3062 publication-title: Adv. Synth. Catal. – volume: 37 start-page: 320 year: 2008 end-page: 330 publication-title: Chem. Soc. Rev. – volume: 17 start-page: 4336 year: 2015 end-page: 4339 publication-title: Org. Lett. – volume: 359 start-page: 1725 year: 2017 end-page: 1734 publication-title: Adv. Synth. Catal. – volume: 56 start-page: 1390 year: 2017 end-page: 1395 publication-title: Angew. Chem. Int. Ed. – volume: 83 start-page: 1661 year: 2018 end-page: 1666 publication-title: J. Org. Chem. – volume: 127 start-page: 992 year: 2006 end-page: 1012 publication-title: J. Fluorine Chem. – volume: 25 start-page: 70 year: 2012 end-page: 85 publication-title: Comprehensive Chirality. – volume: 51 start-page: 4359 year: 2008 end-page: 4369 publication-title: J. Med. Chem. – volume: 77 start-page: 11325 year: 2012 end-page: 11332 publication-title: J. Org. Chem. – volume: 18 start-page: 3154 year: 2016 end-page: 3157 publication-title: Org. Lett. – volume: 51 start-page: 9149 year: 2015 end-page: 9152 publication-title: Chem. Commun. – volume: 110 start-page: 1496 year: 1998 end-page: 1513 publication-title: Angew. Chem. Int. Ed. – start-page: 6401 year: 2015 end-page: 6412 publication-title: Eur. J. Org. Chem. – volume: 18 start-page: 3270 year: 2016 end-page: 3273 publication-title: Org. Lett. – volume: 56 start-page: 7484 year: 2017 end-page: 7487 publication-title: Angew. Chem. Int. Ed. – volume: 115 start-page: 826 year: 2015 end-page: 870 publication-title: Chem. Rev. – ident: e_1_2_6_32_2 doi: 10.1039/C5CC03289J – ident: e_1_2_6_41_1 doi: 10.1002/cmdc.200700059 – ident: e_1_2_6_44_2 doi: 10.1002/anie.201608752 – ident: e_1_2_6_27_2 doi: 10.1021/acs.orglett.7b03713 – ident: e_1_2_6_20_2 doi: 10.1021/acs.orglett.6b01367 – ident: e_1_2_6_18_2 doi: 10.1021/jo502270a – ident: e_1_2_6_13_2 doi: 10.1016/j.jfluchem.2009.09.015 – ident: e_1_2_6_34_1 – ident: e_1_2_6_3_2 doi: 10.1002/(SICI)1521-3773(19980619)37:11<1496::AID-ANIE1496>3.0.CO;2-U – ident: e_1_2_6_24_2 doi: 10.1002/adsc.201700361 – ident: e_1_2_6_19_2 doi: 10.1021/acs.orglett.5b02160 – ident: e_1_2_6_39_2 doi: 10.1039/C6RA27710A – ident: e_1_2_6_47_2 doi: 10.1021/acs.orglett.7b02628 – ident: e_1_2_6_6_2 doi: 10.1080/14756360701425014 – ident: e_1_2_6_22_2 doi: 10.1002/adsc.201700011 – ident: e_1_2_6_42_1 – ident: e_1_2_6_48_1 – ident: e_1_2_6_4_2 doi: 10.1021/jm800219f – ident: e_1_2_6_8_2 doi: 10.1039/B711844A – ident: e_1_2_6_45_1 – ident: e_1_2_6_11_1 – ident: e_1_2_6_38_2 doi: 10.1002/adsc.201700353 – ident: e_1_2_6_14_1 – ident: e_1_2_6_28_1 – ident: e_1_2_6_23_2 doi: 10.1021/acs.orglett.7b02044 – ident: e_1_2_6_46_2 doi: 10.1021/acs.joc.5b02238 – ident: e_1_2_6_25_2 doi: 10.1002/anie.201704086 – ident: e_1_2_6_17_2 doi: 10.1002/adsc.201400581 – ident: e_1_2_6_37_2 doi: 10.1021/acs.orglett.6b01516 – ident: e_1_2_6_15_2 doi: 10.1021/jo302048v – ident: e_1_2_6_5_1 – ident: e_1_2_6_2_1 – ident: e_1_2_6_26_2 doi: 10.1002/anie.201704922 – ident: e_1_2_6_31_2 doi: 10.1002/bkcs.10263 – ident: e_1_2_6_33_2 doi: 10.1002/ejoc.201500787 – ident: e_1_2_6_43_2 doi: 10.1021/cr500277b – ident: e_1_2_6_29_2 doi: 10.1038/86546 – ident: e_1_2_6_36_2 doi: 10.1002/anie.201509719 – ident: e_1_2_6_49_1 doi: 10.1002/adsc.201701198 – ident: e_1_2_6_12_2 doi: 10.1016/j.jfluchem.2006.05.006 – ident: e_1_2_6_7_2 doi: 10.1039/B610213C – ident: e_1_2_6_16_2 doi: 10.1002/adsc.201300373 – ident: e_1_2_6_9_2 doi: 10.4155/fmc.09.70 – ident: e_1_2_6_21_2 doi: 10.1002/adsc.201700353 – ident: e_1_2_6_35_2 doi: 10.1039/C5CC02256H – ident: e_1_2_6_30_2 doi: 10.1039/c3ob41267a – ident: e_1_2_6_10_2 doi: 10.1016/B978-0-08-095167-6.00106-3 – ident: e_1_2_6_40_2 doi: 10.1021/acs.joc.7b03084 – volume: 7 start-page: 5679 year: 2017 ident: WOS:000393754100016 article-title: Asymmetric synthesis of C-F quaternary alpha-fluorob- amino-indolin-2-ones via Mannich addition reactions; facets of reactivity, structural generality and stereochemical outcome publication-title: RSC ADVANCES doi: 10.1039/c6ra27710a – volume: 18 start-page: 3270 year: 2016 ident: WOS:000379455300058 article-title: Detrifluoroacetylative in Situ Generation of Free 3-Fluoroindolin-2-one-Derived Tertiary Enolates: Design, Synthesis, and Assessment of Reactivity toward Asymmetric Mannich Reactions publication-title: ORGANIC LETTERS doi: 10.1021/acs.orglett.6b01516 – volume: 25 start-page: 70 year: 2012 ident: 000441874400024.28 publication-title: Comprehensive Chirality. – volume: 37 start-page: 320 year: 2008 ident: WOS:000252411800007 article-title: Fluorine in medicinal chemistry publication-title: CHEMICAL SOCIETY REVIEWS doi: 10.1039/b610213c – volume: 56 start-page: 1390 year: 2017 ident: WOS:000394997700039 article-title: Catalytic Enantioselective and Diastereoselective Allylic Alkylation with Fluoroenolates: Efficient Access to C3-Fluorinated and All-Carbon Quaternary Oxindoles publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION doi: 10.1002/anie.201608752 – volume: 127 start-page: 992 year: 2006 ident: WOS:000239874500001 article-title: Recent advances (1995-2005) in fluorinated pharmaceuticals based on natural products publication-title: JOURNAL OF FLUORINE CHEMISTRY doi: 10.1016/j.jfluchem.2006.05.006 – volume: 83 start-page: 1661 year: 2018 ident: WOS:000424729400065 article-title: Organocatalytic Stereoselective Synthesis of Fluorinated 3,3 '-Linked Bisoxindoles publication-title: JOURNAL OF ORGANIC CHEMISTRY doi: 10.1021/acs.joc.7b03084 – volume: 56 start-page: 11927 year: 2017 ident: WOS:000410810600046 article-title: Rhodium-Catalyzed Enantioselective Reductive Arylation: Convenient Access to 3,3-Disubstituted Oxindoles publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION doi: 10.1002/anie.201704922 – volume: 11 start-page: 5217 year: 2013 ident: WOS:000322944900003 article-title: Enantioselective conjugate addition of 3-fluorooxindoles to vinyl sulfone: an organocatalytic access to chiral 3-fluoro-3-substituted oxindoles publication-title: ORGANIC & BIOMOLECULAR CHEMISTRY doi: 10.1039/c3ob41267a – volume: 20 start-page: 921 year: 2018 ident: WOS:000426013600007 article-title: Nickel-Catalyzed Domino Heck Cyclization/Suzuki Coupling for the Synthesis of 3,3-Disubstituted Oxindoles publication-title: ORGANIC LETTERS doi: 10.1021/acs.orglett.7b03713 – volume: 18 start-page: 3154 year: 2016 ident: WOS:000379455300029 article-title: Synthesis of Quaternary 3,3-Disubstituted 2-Oxindoles from 2-Substituted Indole Using Selectfluor publication-title: ORGANIC LETTERS doi: 10.1021/acs.orglett.6b01367 – volume: 359 start-page: 1772 year: 2017 ident: WOS:000402839300001 article-title: Recent Catalytic Asymmetric Syntheses of 3,3-Disubstituted Indolin-2-ones and 2,2-Disubstituted Indolin-3-ones publication-title: ADVANCED SYNTHESIS & CATALYSIS doi: 10.1002/adsc.201700361 – volume: 77 start-page: 11325 year: 2012 ident: WOS:000312564900034 article-title: Organocatalyzed Enantioselective Decarboxylative Stereoablation Reaction for the Construction of 3,3 '-Disubstituted Oxindoles Using beta-Ketoacids and 3-Halooxindoles publication-title: JOURNAL OF ORGANIC CHEMISTRY doi: 10.1021/jo302048v – volume: 36 start-page: 1512 year: 2015 ident: WOS:000354133600033 article-title: Organocatalytic Enantioselective Conjugate Addition of 3-Fluorooxindoles to Vinyl Sulfone publication-title: BULLETIN OF THE KOREAN CHEMICAL SOCIETY doi: 10.1002/bkcs.10263 – volume: 359 start-page: 3057 year: 2017 ident: WOS:000408941200020 article-title: Stereoselective Mannich Reaction of N-(tert-Butylsulfinyl) imines with 3-Fluorooxindoles and Fluoroacetamides publication-title: ADVANCED SYNTHESIS & CATALYSIS doi: 10.1002/adsc.201700353 – volume: 55 start-page: 781 year: 2016 ident: WOS:000368069200060 article-title: Catalytic Asymmetric Mannich Reactions with Fluorinated Aromatic Ketones: Efficient Access to Chiral beta-Fluoroamines publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION doi: 10.1002/anie.201509719 – volume: 51 start-page: 10186 year: 2015 ident: WOS:000356021300025 article-title: Enantioselective synthesis of 3-fluoro-3-allyl-oxindoles via phosphine-catalyzed asymmetric gamma-addition of 3-fluoro-oxindoles to 2,3-butadienoates publication-title: CHEMICAL COMMUNICATIONS doi: 10.1039/c5cc03289j – volume: 51 start-page: 4359 year: 2008 ident: WOS:000258289800001 article-title: The many roles for fluorine in medicinal chemistry publication-title: JOURNAL OF MEDICINAL CHEMISTRY doi: 10.1021/jm800219f – volume: 360 start-page: 462 year: 2018 ident: WOS:000424093900013 article-title: Enantioselective Synthesis of beta-Aminotetralins via Chiral Phosphoric Acid-catalyzed Reductive Amination of beta-Tetralones publication-title: ADVANCED SYNTHESIS & CATALYSIS doi: 10.1002/adsc.201701198 – volume: 131 start-page: 127 year: 2010 ident: WOS:000275138300003 article-title: Asymmetric synthesis of fluorine-containing amines, amino alcohols, alpha- and beta-amino acids mediated by chiral sulfinyl group publication-title: JOURNAL OF FLUORINE CHEMISTRY doi: 10.1016/j.jfluchem.2009.09.015 – volume: 17 start-page: 4336 year: 2015 ident: WOS:000361087200054 article-title: Catalytic Asymmetric Four-Component Reaction for the Rapid Construction of 3,3-Disubstituted 3-Indol-3 '-yloxindoles publication-title: ORGANIC LETTERS doi: 10.1021/acs.orglett.5b02160 – volume: 19 start-page: 5336 year: 2017 ident: WOS:000412789600084 article-title: Asymmetric Synthesis of alpha-Fluoro-beta-Amino-oxindoles with Tetrasubstituted C-F Stereogenic Centers via Cooperative Cation Binding Catalysis publication-title: ORGANIC LETTERS doi: 10.1021/acs.orglett.7b02628 – volume: 2 start-page: 1100 year: 2007 ident: WOS:000248851900001 article-title: Predicting properties and tuning physicochemical in lead optimization: Amine basicities publication-title: CHEMMEDCHEM doi: 10.1002/cmdc.200700059 – volume: 56 start-page: 7484 year: 2017 ident: WOS:000403017000025 article-title: Total Synthesis of (+/-)-Corymine publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION doi: 10.1002/anie.201704086 – volume: 355 start-page: 2531 year: 2013 ident: WOS:000327862400009 article-title: Enantioselective Organocatalytic Addition of Nitroalkanes to Oxindolylideneindolenines for the Construction of Chiral 3,3-Disubstituted Oxindoles publication-title: ADVANCED SYNTHESIS & CATALYSIS doi: 10.1002/adsc.201300373 – volume: 1 start-page: 793 year: 2009 ident: WOS:000276093600008 article-title: Practical synthesis of fluorine-containing alpha- and beta-amino acids: recipes from Kiev, Ukraine publication-title: FUTURE MEDICINAL CHEMISTRY doi: 10.4155/FMC.09.70 – volume: 2015 start-page: 6401 year: 2015 ident: WOS:000362749100001 article-title: Recent Progress in the in situ Detrifluoroacetylative Generation of Fluoro Enolates and Their Reactions with Electrophiles publication-title: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY doi: 10.1002/ejoc.201500787 – volume: 115 start-page: 826 year: 2015 ident: WOS:000348689400009 article-title: Advances in Catalytic Enantioselective Fluorination, Mono-, Di-, and Trifluoromethylation, and Trifluoromethylthiolation Reactions publication-title: CHEMICAL REVIEWS doi: 10.1021/cr500277b – volume: 51 start-page: 9149 year: 2015 ident: WOS:000354791400018 article-title: Asymmetric synthesis of quaternary alpha-fluoro-beta-keto-amines via detrifluoroacetylative Mannich reactions publication-title: CHEMICAL COMMUNICATIONS doi: 10.1039/c5cc02256h – volume: 37 start-page: 1496 year: 1998 ident: MEDLINE:29710919 article-title: Parametrization of Substituents: Effects of Fluorine and Other Heteroatoms on OH, NH, and CH Acidities. publication-title: Angewandte Chemie (International ed. in English) doi: 10.1002/(SICI)1521-3773(19980619)37:11<1496::AID-ANIE1496>3.0.CO;2-U – volume: 22 start-page: 527 year: 2007 ident: 000441874400024.26 publication-title: J. Enzyme Inhib. Med. Chem. – volume: 37 start-page: 308 year: 2008 ident: WOS:000252411800006 article-title: Understanding organofluorine chemistry. An introduction to the C-F bond publication-title: CHEMICAL SOCIETY REVIEWS doi: 10.1039/b711844a – volume: 359 start-page: 1725 year: 2017 ident: WOS:000401528100017 article-title: Chiral Squaramide-Catalyzed Enantioselective Decarboxylative Addition of -Keto Acids to Isatin Imines publication-title: ADVANCED SYNTHESIS & CATALYSIS doi: 10.1002/adsc.201700011 – volume: 7 start-page: 471 year: 2001 ident: WOS:000167960500043 article-title: Targeting acute ischemic stroke with a calcium-sensitive opener of maxi-K potassium channels publication-title: NATURE MEDICINE – volume: 356 start-page: 2919 year: 2014 ident: WOS:000342906100004 article-title: alpha,alpha-Dichlorination of Oxindole Derivatives Using (Dichloroiodo)-benzene publication-title: ADVANCED SYNTHESIS & CATALYSIS doi: 10.1002/adsc.201400581 – volume: 80 start-page: 634 year: 2015 ident: WOS:000347506400065 article-title: Preparation of 3-Sulfonylated 3,3-Disubstituted Oxindoles by the Addition of Sulfinate Salts to 3-Halooxindoles publication-title: JOURNAL OF ORGANIC CHEMISTRY doi: 10.1021/jo502270a – volume: 19 start-page: 4351 year: 2017 ident: WOS:000408285600050 article-title: Development of Biligands Magnesium Catalysis in Asymmetric Conjugate Reactions of C3-Pyrrolyl-Oxindoles publication-title: ORGANIC LETTERS doi: 10.1021/acs.orglett.7b02044 – volume: 80 start-page: 12651 year: 2015 ident: WOS:000366877900077 article-title: Construction of Vicinal Tetrasubstituted Stereocenters with a C-F Bond through a Catalytic Enantioselective Detrifluoroacetylative Mannich Reaction publication-title: JOURNAL OF ORGANIC CHEMISTRY doi: 10.1021/acs.joc.5b02238 |
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| Snippet | A squaramide‐catalyzed asymmetric Mannich reaction of 3‐fluorooxindoles to isatin‐derived imines for synthesis of fluorinated 3,3′‐bisoxindoles with two... A squaramide-catalyzed asymmetric Mannich reaction of 3-fluorooxindoles to isatin-derived imines for synthesis of fluorinated 3,3-bisoxindoles with two... |
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| SubjectTerms | Asymmetric catalysis Bisoxindoles Chemical reactions Chemical synthesis Chemistry Chemistry, Applied Chemistry, Organic Fluorination Imines Mannich addition Organocatalysis Physical Sciences Science & Technology Squaramides Stereoselectivity |
| Title | Chiral Squaramide‐Catalyzed Asymmetric Mannich Reactions for Synthesis of Fluorinated 3,3′‐Bisoxindoles |
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