Synthesis
DOI: 10.1055/a-2376-3524
review
Special Topic Dedicated to Prof. H. Ila

Organocatalytic Approaches Towards the Synthesis of Asymmetric Tetrahydroquinoline (THQ) Derivatives

Kamal Kant
a   Department of Chemistry, National Institute of Technology Manipur, Imphal – 795004, India
,
Priyadarshini Naik
a   Department of Chemistry, National Institute of Technology Manipur, Imphal – 795004, India
,
Chandresh Kumar Patel
a   Department of Chemistry, National Institute of Technology Manipur, Imphal – 795004, India
,
Sanjukta Some
a   Department of Chemistry, National Institute of Technology Manipur, Imphal – 795004, India
,
Sourav Banerjee
a   Department of Chemistry, National Institute of Technology Manipur, Imphal – 795004, India
,
Nayyef Aljaar
b   Department of Chemistry, Faculty of Science, The Hashemite University, P.O. Box 330127, Zarqa – 13133, Jordan
,
Ananta K. Atta
c   Department of Chemistry, National Institute of Technology Jamshedpur, Adityapur, Jharkhand 831014, India
,
a   Department of Chemistry, National Institute of Technology Manipur, Imphal – 795004, India
› Author Affiliations
C.C.M. appreciates the Science and Engineering Research Board (SERB), New Delhi (Grants No. CRG/2020/004509 and ECR/2016/000337), and NIT Manipur for financial support. K.K. and C.K.P. are grateful to the Ministry of Education (MoE), New Delhi for fellowship support.


Abstract

1,2,3,4-Tetrahydroquinolines (THQs) are present in molecules with significant biological importance and pharmaceuticals with diverse biological activities. Various synthetic routes have been developed to tetrahydroquinolines, such as the hydrogenation of quinolines, domino reactions, intramolecular cyclization, and notably, the Povarov reaction. Organocatalysts are small, chiral organic molecules that can successfully catalyze organic transformations. This review examines the use of organocatalysts in the asymmetric synthesis of tetrahydroquinoline derivatives using aminocatalysis, NHC catalysis, and H-bonding catalysis covering the literature between 2000 and early 2024.

1 Introduction

2 Aminocatalysis

3 NHC Catalysis

4 H-Bonding Catalysis

5 Miscellaneous

6 Conclusion



Publication History

Received: 31 May 2024

Accepted after revision: 30 July 2024

Accepted Manuscript online:
30 July 2024

Article published online:
25 September 2024

© 2024. Thieme. All rights reserved

Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany

 
  • References

  • 1 Cosgrove SC, Hussain S, Turner NJ, Marshden SP. ACS Catal. 2018; 8: 5570
    • 2a Muthukrishnan I, Sridharan V, Menendez JC. Chem. Rev. 2019; 119: 5057
    • 2b Sridharan V, Suryavanshi P, Menendez JC. Chem. Rev. 2011; 111: 7157
    • 2c Kouznetsov V, Palma A, Ewert C, Varlamov A. J. Heterocycl. Chem. 1998; 35: 761
    • 2d Katritzky AR, Rachwal S, Rachwal B. Tetrahedron 1996; 52: 15031
    • 2e Ramesh M, Acharya A, Murugan NA, Ila H, Govindaraju T. ChemBioChem 2021; 22: 3348
    • 2f Putta VP. R. K, Gujjarappa R, Vodnala N, Gupta R, Pujar PP, Malakar CC. Tetrahedron Lett. 2018; 59: 904
    • 2g Putta VP. R. K, Vodnala N, Gujjarappa R, Tyagi U, Garg A, Gupta S, Pujar PP, Malakar CC. J. Org. Chem. 2020; 85: 380
    • 2h Gujjarappa R, Vodnala N, Musib D, Malakar CC. Asian J. Org. Chem. 2022; 11: e202100627
    • 2i Antony PM, Balaji GL, Iniyavan P, Ila H. J. Org. Chem. 2020; 85: 15422
    • 2j Avadhani A, Iniyavan P, Kumar Y, Ila H. J. Org. Chem. 2021; 86: 8508
    • 2k Aljaar N, Ibrahim MM, Younes EA, Al-Noaimi M, Abu-Safieh KA, Ali BF, Kant K, Al-Zaqri N, Sengupta R, Malakar CC. Asian J. Org. Chem. 2023; 12: e202300036
    • 2l Patel CK, Banerjee S, Kant K, Sengupta R, Aljaar N, Malakar CC. Asian J. Org. Chem. 2023; 12: e202300311
    • 2m Patel CK, Gujjarappa R, Kant K, Ghanta S, Singh V, Kabi AK, Al-Zaqri N, Malakar CC. Adv. Synth. Catal. 2023; 365: 2203
    • 2n Devi EP, Polina S, Kant K, Kabi AK, Al-Zaqri N, Aljaar N, Malakar CC. Heterocycles 2023; 106: 1023
    • 2o Kant K, Patel CK, Banerjee S, Naik P, Atta AK, Kabi AK, Malakar CC. ChemistrySelect 2023; 8: e202303988
    • 2p Aljaar N, Gujjarappa R, Al-Refai M, Shtaiwi M, Malakar CC. J. Heterocycl. Chem. 2019; 56: 2730
    • 2q Kushwaha K, Pinter B, Shehzadi SA, Malakar CC, Vande CM, Proft FD, Tehrani KA. Adv. Synth. Catal. 2016; 358: 41
    • 2r Acharya A, Kumar SV, Ila H. Chem. Eur. J. 2015; 21: 17116
    • 2s Patel CK, Kant K, Teli YA, Banerjee S, Naik P, Sharma V, Keremane KS, Al-Sadoon MK, Singh V, Malakar CC. Asian J. Org. Chem. 2024; in press DOI: 10.1002/ajoc.202400255.
    • 2t Kant K, Patel CK, Banerjee S, Naik P, Padhi A, Sharma V, Singh V, Almeer R, Keremane KS, Atta AK, Malakar CC. Asian J. Org. Chem. 2024; in press DOI: 10.1002/ajoc.202400223.
    • 3a Witherup KM, Rausom RW, Graham AC, Bernard AM, Salvatore MJ, Lumma WC, Anderson PS, Pitzenberger SM, Varga SL. J. Am. Chem. Soc. 1995; 117: 6682
    • 3b Nyerges M. Heterocycles 2004; 63: 1685
    • 3c Lovely CJ, Badarinarayana V. Curr. Org. Chem. 2008; 12: 1431
    • 3d Rakotoson JH, Fabre N, Jacquemond-Collet I, Hannedouche S, Fouraste I, Moulis C. Planta Med. 1998; 64: 762
    • 3e Houghton PJ, Woldemariam TZ, Watanabe Y, Yates M. Planta Med. 1999; 65: 250
    • 3f Jacquemond-Collet I, Hannedouche S, Fabre N, Fouraste I, Moulis C. Phytochemistry 1999; 51: 1167
    • 3g Jacquemond-Collet I, Bessiere J.-M, Hannedouche S, Bertrand C, Fouraste I, Moulis C. Phytochem. Anal. 2001; 12: 312
    • 4a Bedoya LM, Abad MJ, Calonge E, Astudillo-Saavedra L, Gutierrez CM, Kouznetsov VV, Alcami J, Bermejo P. Antiviral Res. 2010; 87: 338
    • 4b Cole AG, Metzger A, Brescia MR, Qjn L.-Y, Appell KC, Brain CT, Hallett A, Ganju P, Denholm AA, Wareing JR, Ritchie TJ, Drake GM, Bevan SJ, MacGloinn A, McBryde A, Patel V, Oakley PJ, Nunez X, Gstach H, Schneider P, Baldwin JJ, Dolle RE, McDonald E, Henderson I. Bioorg. Med. Chem. Lett. 2009; 19: 119
    • 4c Su D.-S, Lim JJ, Tinney E, Wan B.-L, Young MB, Anderson KD, Rudd D, Munshi V, Bahnck C, Felock PJ, Lu M, Lai M.-T, Touch S, Moyer G, DiStefano DJ, Flynn JA, Liang Y, Sanchez R, Prasad S, Yan Y, Perlow-Poehnelt R, Torrent M, Miller M, Vacca JP, Williams TM, Anthony NJ. Bioorg. Med. Chem. Lett. 2009; 19: 5119
    • 4d Zhang J, Zhan P, Wu J, Li Z, Jiang Y, Ge W, Pannecouque C, De Clercq E, Liu X. Bioorg. Med. Chem. 2011; 19: 4366
    • 4e Chander S, Wang P, Ashok P, Yang L.-M, Zheng Y.-T, Murugesan S. Bioorg. Chem. 2016; 67: 75
    • 5a Dhanapal R, Perumal PT, Sridhar R. Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem. 2014; 53: 193
    • 5b Kumar A, Srivastava S, Gupta G, Chaturvedi V, Sinha S, Srivastava R. ACS Comb. Sci. 2011; 13: 65
    • 5c Kantevari S, Yempala T, Surineni G, Sridhar B, Yogeeswari P, Sriram D. Eur. J. Med. Chem. 2011; 46: 4827
    • 5d Dhanapal R, Perumal PT, Damodiran M, Ramprasath C, Mathivanan N. Bioorg. Med. Chem. Lett. 2012; 22: 6494
    • 6a Kraub J, Hornacek M, Müller C, Staudacher V, Stadler M, Bracher F. Sci. Pharm. 2015; 83: 1
    • 6b Gutierrez M, Carmona U, Vallejos G, Astudillo L. J. Biosci. 2012; 67: 551
    • 6c Romero-Bohórquez AR, Kouznetsov VV, Zacchino SA. Univ. Sci. (Pontif. Univ. Javeriana, Fac. Cienc.) 2014; 20: 177
    • 7a Fonseca-Berzal C, Merchan-Arenas DR, Romero-Bohórquez AR, Escario JA, Kouznetsov VV, Gomez-Barrio A. Bioorg. Med. Chem. Lett. 2013; 23: 4851
    • 7b Romero-Bohórquez AR, Escobar-Rivero P, Leal SM, Kouznetsov VV. Lett. Drug Des. Discovery 2012; 9: 802
    • 7c Pagliero RJ, Lusvarghi S, Pierini AB, Brun R, Mazzieri MR. Bioorg. Med. Chem. 2010; 18: 142
    • 8a Jo H, Choi M, Kumar AS, Jung Y, Kim S, Yun J, Kang J.-S, Kim Y, Han S.-B, Jung J.-K, Cho J, Lee K, Kwak J.-H, Lee H. ACS Med. Chem. Lett. 2016; 7: 385
    • 8b Lam K.-H, Lee KK.-H, Gambari R, Wong RS.-M, Cheng GY.-M, Tong S.-W, Chan K.-W, Lau F.-Y, Lai PB.-S, Wong W.-Y, Chan AS.-C, Kok SH.-L, Tang JC.-O, Chui C.-H. Phytomedicine 2013; 20: 166
    • 8c Wang X.-F, Wang S.-B, Ohkoshi E, Wang L.-T, Hamel E, Qian K, Morris-Natschke SL, Lee K.-H, Xie L. Eur. J. Med. Chem. 2013; 67: 196
    • 8d Wang SB, Wang X.-F, Qin B, Ohkoshi E, Hsieh K.-Y, Hamel E, Cui M.-T, Zhu DQ, Goto M, Morris-Natschke SL, Lee K.-H, Xie L. Bioorg. Med. Chem. 2015; 23: 5740
    • 8e Muiioz A, Sojo F, Merchan-Arenas D, Kouznetsov VV, Arvelo F. Chem.-Biol. Interact. 2011; 189: 215
    • 8f Kouznetsov VV, Merchan-Arenas D, Tangarife-Castaño V, Correa-Royero J, Betancur-Galvis L. Med. Chem. Res. 2016; 25: 429
    • 8g Nagaiah K, Venkatesham A, Rao RS, Saddanapu V, Yadav JS, Basha SJ, Sharma AV. S, Sridhar B, Addlagatta A. Bioorg. Med. Chem. Lett. 2010; 20: 3259
    • 9a Wu Q, Li Y, Yang X, Ling Y. Youji Huaxue 2012; 32: 1498
    • 9b Wu Q, Li Y, Yang X, Ling Y. Youji Huaxue 2012; 32: 747
    • 9c Lei P, Zhang X, Xu Y, Xu G, Liu X, Yang X, Zhang X, Ling Y. Chem. Cent. J. 2016; 10: 40
    • 9d Mack DJ, Isoe J, Miesfeld RL, Njardarson JT. Bioorg. Med. Chem. Lett. 2012; 22: 5177
    • 9e Kitamura S, Harada T, Hiramatsu H, Shimizu R, Miyagawa H, Nakagawa Y. Bioorg. Med. Chem. Lett. 2014; 24: 1715
  • 10 Niewiarowska-Sendo A, Kozik A, Guevara-Lora I. Plos One 2018; 13: e0206443
  • 11 Zhang S, Xia Z, Ni T, Zhang H, Wu C, Qu Y. J. Mater. Chem. A 2017; 5: 3260
  • 12 Zhou YG. Acc. Chem. Res. 2007; 40: 1357
    • 13a Das S, Chakrabarty S, Daniliuc CG, Studer A. Org. Lett. 2016; 18: 2784
    • 13b Maurya RK, Patel OP. S, Anand D, Yadav PP. Org. Chem. Front. 2018; 5: 1170
    • 13c Bai P, Li YQ, Huang ZZ. Org. Lett. 2017; 19: 1374
    • 13d Han JQ, Zhang HH, Xu PF, Luo YC. Org. Lett. 2016; 18: 5212
    • 14a Alt IT, Guttroff C, Plietker B. Angew. Chem. Int. Ed. 2017; 56: 10582
    • 14b Youn TH, Kim DY. Synth. Commun. 2017; 47: 2109
    • 14c Pan Z, Pound SM, Rondla NR, Douglas CJ. Angew. Chem. Int. Ed. 2014; 53: 5170
    • 14d Kang YK, Kim SM, Kim DY. J. Am. Chem. Soc. 2010; 132: 11847
    • 14e Briones JF, Basarab GS. Chem. Commun. 2016; 52: 8541
    • 14f Han YY, Han WY, Hou X, Zhang XM, Yuan WC. Org. Lett. 2012; 14: 4054
    • 14g Liu W, Zhou P, Lang J, Dong S, Liu X, Feng X. Chem. Commun. 2019; 55: 4479
    • 14h Cao W, Liu X, Wang W, Lin L, Feng X. Org. Lett. 2011; 13: 600
  • 15 Ghashghaei O, Masdeu C, Alonso C, Palacios F, Lavilla R. Drug Discovery Today: Technol. 2018; 29: 71
    • 16a Mitchinson A, Nadin A. J. Chem. Soc., Perkin Trans. 1 1999; 2553
    • 16b Mitchenson A, Nadin A. J. Chem. Soc., Perkin Trans. 1 2000; 2862
    • 16c Nammalwar B, Bunce RA. Molecules 2014; 19: 204
    • 16d Jacquemond-Collet I, Benoit-Vical F, Valentin MA, Stanislas E, Mallie M, Fouraste I. Planta Med. 2002; 68: 68
    • 16e Davies SG, Fletcher AM, Houlsby IT. T, Roberts PM, Thomson JE. J. Org. Chem. 2017; 82: 10673
    • 17a Cheong PH.-Y, Legault CY, Um JM, Celebi-Ölcum N, Houk KN. Chem. Rev. 2011; 111: 5042
    • 17b Vicario JL, Reyes E, Carrillo L, Uria U. Organocatalytic Asymmetric Nucleophilic Addition to Electron-Deficient Alkenes. In Comprehensive Organic Synthesis II, Vol. 4. Knochel P. Elsevier; Amsterdam: 2014: 119
  • 18 Fustero S, Moscardó J, Jiménez D, Pérez-Carrión MD, Sánchez-Roselló M, del Pozo C. Chem. Eur. J. 2008; 14: 9868
  • 19 Gu J, Xiao B.-X, Chen Y.-R, Du W, Chen Y.-C. Adv. Synth. Catal. 2016; 358: 296
  • 20 Kim MH, Kim DY. Bull. Korean Chem. Soc. 2013; 34: 3891
  • 21 Dai L, Hou Y, Chen LZ, Zeng X, Zhong G. Org. Biomol. Chem. 2017; 15: 9630
  • 22 Geng Z.-C, Zhang S.-Y, Ning N.-K, Li N, Chen J, Li H.-Y, Wang X.-W. J. Org. Chem. 2014; 79: 10772
  • 23 Huang J.-X, Hou K.-Q, Hu Q.-L, Chen X.-P, Li J, Chan AS. C, Xiong X.-F. Org. Lett. 2020; 22: 1858
  • 24 Leth LA, Glaus F, Meazza M, Fu L, Thogersen MK, Bitsch EA, Jørgensen KA. Angew. Chem. Int. Ed. 2016; 55: 15272
  • 25 Lin H, Sun X.-W, Lin G.-Q. Org. Lett. 2014; 16: 752
  • 26 Tian J.-M, Yuan Y.-H, Xie Y.-Y, Zhang S.-Y, Ma W.-Q, Zhang F.-M, Wang S.-H, Zhang X.-M, Tu Y.-Q. Org. Lett. 2017; 19: 6618
  • 27 Suh WC, Kim YD. Org. Lett. 2014; 16: 5374
  • 28 Kim C, Kim S.-G. Tetrahedron: Asymmetry 2014; 25: 1376
  • 29 Rajanarendar E, Reddy MN, Reddy KG, Krishna SR. Tetrahedron Lett. 2012; 53: 2909
  • 30 Lu H.-H, Liu H, Wu W, Wan X.-F, Lu L.-Q, Xiao W.-J. Chem. Eur. J. 2009; 15: 2742
  • 31 Wu H, Wang Y.-M. Chem. Eur. J. 2014; 20: 5899
  • 32 Devakaram R, Black DSt. C, Kumar N. Tetrahedron Lett. 2012; 53: 2269
  • 33 Heo S, Kim S, Kim S.-G. Tetrahedron Lett. 2013; 54: 4978
  • 34 Lee Y, Kim S. J. Org. Chem. 2014; 79: 8234
  • 35 Garg Y, Gahalawat S, Pandey KS. RSC Adv. 2015; 5: 38846
  • 36 Gwon SH, Kim SG. Tetrahedron: Asymmetry 2012; 23: 1251
  • 37 Rawat V, Kumar BS, Sudalai A. Org. Biomol. Chem. 2013; 11: 3608
  • 38 Kang YK, Kim DY. Chem. Commun. 2014; 50: 222
  • 39 Wu X, Chen D, Chen S, Zhu Y. Eur. J. Org. Chem. 2015; 2015: 468
  • 40 Zhang XL, Feng KX, Hu JL, Shen QY, Huang WS, Xia AB, Li C, Xu DQ. New J. Chem. 2021; 45: 1168
  • 41 Jia M.-Q, You S.-L. ACS Catal. 2013; 3: 622
  • 42 Lee A, Younai A, Price CK, Izquierdo J, Mishra RK, Scheidt KA. J. Am. Chem. Soc. 2014; 136: 10589
  • 43 Zhang H.-R, Dong Z.-W, Yang Y.-J, Wang P.-L, Hui X.-P. Org. Lett. 2013; 15: 4750
  • 44 Bisag GD, Pecorari D, Mazzanti A, Bernardi L, Fochi M, Bencivenni G, Bertuzzi G, Corti V. Chem. Eur. J. 2019; 25: 15694
  • 45 Rueping M, Theissmann T, Stoeckel M, Antonchick AP. Org. Biomol. Chem. 2011; 9: 6844
  • 46 Caruana L, Fochi M, Ranieri S, Mazzanti A, Bernardi L. Chem. Commun. 2013; 49: 880
  • 47 He L, Bekkaye M, Retailleau P, Masson G. Org. Lett. 2012; 14: 3158
  • 48 Jarrige L, Blanchard F, Masson G. Angew. Chem. Int. Ed. 2017; 56: 10573
  • 49 Lin J.-H, Zong G, Du R.-B, Xiao J.-C, Liu S. Chem. Commun. 2012; 48: 7738
  • 50 Jarrige L, Gandon V, Masson G. Chem. Eur. J. 2020; 26: 1406
  • 51 Ren L, Lei T, Ye J.-X, Gong L.-Z. Angew. Chem. Int. Ed. 2012; 51: 771
  • 52 Li L.-Z, Wang C.-S, Guo W.-F, Mei G.-J, Shi F. J. Org. Chem. 2018; 83: 614
  • 53 Li J, Gu Z, Zhao X, Qiao B, Jiang Z. Chem. Commun. 2019; 55: 12916
  • 54 Kazancioglu MZ, Kalay E, Kazancioglu EA, Peshkov VA. ChemistrySelect 2019; 4: 8797
  • 55 Liao H.-H, Hsiao C.-C, Atodiresei I, Rueping M. Chem. Eur. J. 2018; 24: 7718
  • 56 Zhang H.-H, Sun X.-X, Liang J, Wang Y.-M, Zhao C.-C, Shi F. Org. Biomol. Chem. 2014; 12: 9539
  • 57 Liu H, Dagousset G, Masson G, Retailleau P, Zhu J. J. Am. Chem. Soc. 2009; 131: 4598
  • 58 Liao H.-H, Hsiao C.-C, Sugiono E, Rueping M. Chem. Commun. 2013; 49: 7953
  • 59 Akiyama T, Morita H, Fuchibe K. J. Am. Chem. Soc. 2006; 128: 13070
  • 60 Min C, Seidel D. Chem. Eur. J. 2016; 22: 10817
  • 61 Luo C, Huang Y. J. Am. Chem. Soc. 2013; 135: 8193
  • 62 Huang D, Xu F, Chen T, Wang Y, Lin X. RSC Adv. 2013; 3: 573
  • 63 Stevanović D, Bertuzzi G, Mazzanti A, Fochi M, Bernardi L. Adv. Synth. Catal. 2018; 360: 893
  • 64 Sugiono E, Rueping M. Beilstein J. Org. Chem. 2013; 9: 2457
  • 65 Shi F, Xing G.-J, Tao Z.-L, Luo S.-W, Tu S.-J, Gong L.-Z. J. Org. Chem. 2012; 77: 6970
  • 66 Bergongini G, Gramigna L, Mazzanti A, Fochi M, Bernardi L, Ricci A. Chem. Commun. 2010; 46: 327
  • 67 Dagousset G, Zhu J, Masson G. J. Am. Chem. Soc. 2011; 133: 14804
  • 68 Dagousset G, Retailleau P, Masson G, Zhu J. Chem. Eur. J. 2012; 18: 5869
  • 69 Wang S, Zhang W, You S. Org. Lett. 2013; 15: 1488
  • 70 Dai W, Jiang X, Tao J, Shi F. J. Org. Chem. 2016; 81: 185
  • 71 Chen Z, Wang B, Wang Z, Zhu G, Sun J. Angew. Chem. Int. Ed. 2013; 52: 2027
  • 72 Chen Y, Zhu C, Guo Z, Liu W, Yang X. Angew. Chem. Int. Ed. 2021; 60: 5268
  • 73 Yang W, Du D. Chem. Commun. 2013; 49: 8842
  • 74 Zhu Y, Li B, Wang C, Dong Z, Zhong X, Wang K, Yan W, Wang R. Org. Biomol. Chem. 2017; 15: 4544
  • 75 Cheng S, Zhao L, Yu S. Adv. Synth. Catal. 2014; 356: 982
  • 76 Jia Z, Luo Y, Xu P. Org. Lett. 2011; 13: 832
  • 77 Fustero S, del Pozo C, Mulet C, Lazaro R, Sánchez-Roselló M. Chem. Eur. J. 2011; 17: 14267
  • 78 Song Y, Du D.-M. Org. Biomol. Chem. 2018; 16: 9390
  • 79 Min C, Mittal N, Sun DX, Seidel D. Angew. Chem. Int. Ed. 2013; 52: 14084
  • 80 Min C, Lin C.-T, Seidel D. Angew. Chem. Int. Ed. 2015; 54: 6608
  • 81 Ramachary DB, Shruthi KS. Org. Biomol. Chem. 2014; 12: 4300
  • 82 Filatova EV, Turova OV, Nigmatov AG, Zlotin SG. Tetrahedron 2018; 74: 157
  • 83 Tan HR, Ng HF, Chang J, Wang J. Chem. Eur. J. 2012; 18: 3865
  • 84 Engl OD, Fritz SP, Käslin A, Wennemers H. Org. Lett. 2014; 16: 5454
  • 85 Jeong HI, Youn TH, Kim DY. Bull. Korean Chem. Soc. 2017; 38: 421
  • 86 Huang Y, Qiu Q, Li Z, Feng W, Gan H, Liu J, Guo K. ACS Sustainable Chem. Eng. 2016; 4: 47
  • 87 Mao H, Lin A, Tang Y, Shi Y, Hu H, Cheng Y, Zhu C. Org. Lett. 2013; 15: 4062
  • 88 Xiao X, Liu X, Dong S, Cai Y, Lin L, Feng X. Chem. Eur. J. 2012; 18: 15922