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Synthesis 2021; 53(19): 3564-3572
DOI: 10.1055/a-1493-6420
DOI: 10.1055/a-1493-6420
feature
Iron-Catalyzed Stereoselective Allylboration of 3,4-Dihydroisoquinolines with Potassium Allyltrifluoroborates
The authors thank the financial support from Hefei University of Technology and Fundamental Research Funds for the Central Universities.
Abstract
An iron-catalyzed allyation of isoquinoline with potassium allyltrifluoroborate is described. The operation of this reaction is very simple and highly practical. The diastereoisomer having two adjacent chiral centers were obtained in single anti-configuration.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-1493-6420. Included are NMR spectra and the crystal structures of compounds 3lc and 3ld.
- Supporting Information
Primary Data
- Primary Data
Primary data for this article are available online at https://zenodo.org/record/4771250 and can be cited using the following DOI: 10.5281/zenodo.4771250.
Publication History
Received: 14 March 2021
Accepted after revision: 28 April 2021
Accepted Manuscript online:
28 April 2021
Article published online:
25 May 2021
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References
- 1a Ramadhar TR, Batey RA. Synthesis 2011; 1321
- 1b Diner C, Szabó K. J. Am. Chem. Soc. 2017; 139: 2
- 1c Huo H-X, Duvall JR, Huang M-Y, Hong R. Org. Chem. Front. 2014; 1: 303
- 1d Yus M, González-Gómez JC, Foubelo F. Chem. Rev. 2013; 113: 5595
- 2a Meller A, Gerger W. Monatsh. Chem. 1974; 105: 684
- 2b Bubnov YN, Zhun’ IV, Klimkina EV, Ignatenko AV, Starikova ZA. Eur. J. Org. Chem. 2000; 3323
- 2c Yamamoto Y, Komatsu T, Maruyama KJ. J. Org. Chem. 1985; 50: 3115
- 2d Watanabe K, Ito K, Itsuno S. Tetrahedron: Asymmetry 1995; 6: 1531
- 3a Hoffmann RW, Eichler G, Endesfelder A. Liebigs Ann. Chem. 1983; 2000
- 3b Wuts PG. M, Jung Y.-W. J. Org. Chem. 1991; 56: 365
- 3c Sieber JD, Morken JP. J. Am. Chem. Soc. 2006; 128: 74
- 3d Wu TR, Chong JM. J. Am. Chem. Soc. 2006; 128: 9646
- 3e Chen JL. Y, Aggarwal VK. Angew. Chem. Int. Ed. 2014; 53: 10992
- 3f Liu J, Tong X, Chen M. J. Org. Chem. 2020; 85: 5193
- 3g Ullrich P, Schmauck J, Brauns M, Mantel M, Breugst M, Pietruszka J. J. Org. Chem. 2020; 85: 1894
- 4a Dhudshia B, Tiburcio J, Thadani AN. Chem. Commun. 2005; 5551
- 4b Das A, Alam R, Eriksson L, Szabó KJ. Org. Lett. 2014; 16: 3808
- 4c Alam R, Das A, Huang G, Eriksson L, Himo F, Szabá KJ. Chem. Sci. 2014; 5: 2732
- 5a Wada R, Shibuguchi T, Makino S, Oisaki K, Kanai M, Shibasaki M. J. Am. Chem. Soc. 2006; 128: 7687
- 5b Lou S, Moquist PN, Schaus SE. J. Am. Chem. Soc. 2007; 129: 15398
- 5c Fujita M, Nagano T, Schneider U, Hamada T, Ogawa C, Kobayashi S. J. Am. Chem. Soc. 2008; 130: 2914
- 5d Schneider U, Chen I, Kobayashi S. Org. Lett. 2008; 10: 737
- 5e Chakrabarti A, Konishi H, Yamaguchi M, Schneider U, Kobayashi S. Angew. Chem. Int. Ed. 2010; 49: 1838
- 5f Barker TJ, Jarvo ER. Org. Lett. 2009; 11: 1047
- 5g Vieira EM, Snapper ML, Hoveyda AH. J. Am. Chem. Soc. 2011; 133: 3332
- 5h Silverio DL, Torker S, Pilyugina T, Vieira EM, Snapper ML, Haeffner F, Hoveyda AH. Nature 2013; 494: 216
- 5i van der Mei FW, Miyamoto H, Silverio DL, Hoveyda AH. Angew. Chem. Int. Ed. 2016; 55: 4701
- 5j Morrison RJ, Hoveyda AH. Angew. Chem. Int. Ed. 2018; 57: 11654
- 5k Yasumoto K, Kano T, Maruoka K. Org. Lett. 2019; 21: 3214
- 5l Cai L, Pan Y.-L, Chen L, Cheng J.-P, Li X. Chem. Commun. 2020; 56: 12383
- 6 For catalytic allylboration of imines using allylboronic acids, see: Alam R, Diner C, Jonker S, Eriksson L, Szabo KJ. Angew. Chem. Int. Ed. 2016; 55: 14417
- 7 BF3-catalyzed allylboration of imines using potassium allyltrifluoroborates: Li S.-W, Batey RA. Chem. Commun. 2004; 1382
- 8 Allylboration of imines using potassium allyltrifluoroborates: Nowrouzi F, Batey RA. Angew. Chem. Int. Ed. 2013; 52: 892
- 9 Pd-catalyzed allylboration of imines using potassium allyltrifluoroborates: Solin N, Wallner OA, Szabó KJ. Org. Lett. 2005; 7: 689
- 10a Luo Y, Hepburn HB, Chotsaeng N, Lam HM. Angew. Chem. Int. Ed. 2012; 51: 8309
- 10b Hepburn HB, Chotsaeng N, Luo Y, Lam HW. Synthesis 2013; 45: 2649
- 10c Hepburn HB, Lam HW. Angew. Chem. Int. Ed. 2014; 53: 11605
- 10d Martínez JI, Smith JJ, Hepburn HB, Lam HW. Angew. Chem. Int. Ed. 2016; 55: 1108
- 10e Chiang P.-F, Li W.-S, Jian J.-H, Kuo T.-S, Wu P.-Y, Wu H.-L. Org. Lett. 2018; 20: 158
- 10f Li W.-S, Kuo T.-S, Hsieh M.-C, Tsai M.-K, Wu P.-Y, Wu H.-L. Org. Lett. 2020; 22: 5675
- 11a Chrzanowska M, Grajewska A, Rozwadowska MD. Chem. Rev. 2016; 116: 12369
- 11b Liu W, Liu S, Jin R, Guo H, Zhao J. Org. Chem. Front. 2015; 2: 288
- 12a Dunsmore CJ, Carr R, Fleming T, Turner NJ. J. Am. Chem. Soc. 2006; 128: 2224
- 12b Ghislieri D, Houghton D, Green AP, Willies SC, Turner NJ. ACS Catal. 2013; 3: 2869
- 12c Li C, Xiao J. J. Am. Chem. Soc. 2008; 130: 13208
- 12d Zhang G, Zhang Y, Wang R. Angew. Chem. Int. Ed. 2011; 50: 10429
- 12e Ji Y, Shi L, Chen M, Feng G, Zhou Y. J. Am. Chem. Soc. 2015; 137: 10496
- 12f Reddy YV, Biradar DO, Reddy BJ. M, Rathod A, Himabindu M, Reddy BV. S. Nat. Prod. Commun. 2017; 12: 1599
- 12g Zhou H, Liu Y, Yang S, Zhou L, Chang M. Angew. Chem. Int. Ed. 2017; 56: 2725
- 12h Qian G, Bai M, Gao S, Chen H, Zhou S, Cheng HG, Yan W, Zhou Q. Angew. Chem. Int. Ed. 2018; 57: 10980
- 12i Qi L, Hou H, Ling F, Zhong W. Org. Biomol. Chem. 2018; 16: 566
- 12j Fang S.-L, Jiang M.-X, Zhang S, Wu Y.-J, Shi B.-F. Org. Lett. 2019; 21: 4609
- 12k Gil-Negrete JM, Sestelo JP, Sarandeses LA. J. Org. Chem. 2019; 84: 9778
- 12l Jia J, Chen R, Jia Y, Gu H, Zhou Q, Chen X. J. Org. Chem. 2019; 84: 13696
- 12m Kim AN, Ngamnithiporn A, Welin ER, Daiger MT, Grünanger CU, Bartberger MD, Virgil SC, Stoltz BM. ACS Catal. 2020; 10: 3241
- 12n Yang L, Zhu J, Sun C, Deng Z, Qu X. Chem. Sci. 2020; 11: 364
- 12o Li W.-S, Kuo T.-S, Wu P.-Y, Chen C.-T, Wu H.-L. Org. Lett. 2021; 23: 1141
- 12p Ortiz Villamizar MC, Puerto Galvis CE, Kouznetsov VV. Synthesis 2021; 53: 547
- 13 Yanagisawa A, Ogasawara K, Yasue K, Yamamoto H. Chem. Commun. 1996; 367
- 14 Miyazaki M, Ando N, Sugai K, Seito Y, Fukuoka H, Kanemitsu T, Nagata K, Odanaka Y, Nakamura KT, Itoh T. J. Org. Chem. 2011; 76: 534
- 15 For a comprehensive review about iron catalysis, see: Bauer I, Knölker H.-J. Chem. Rev. 2015; 115: 3170
For reviews, see:
For examples of allylboration of imines using allylboranes, see:
For examples of allylboration of imines using allylborates, see:
For examples of allylboration of imines using allylboronic acids, see:
For the catalytic allylboration of imines using allylboronates or boronic acids, see:
Rh-catalyzed allylboration of imines using potassium allyltrifluoroborates:
For reviews, see:
Recent examples of miscellaneous synthetic protocol for preparing chiral tetrahydroisoquinolines: