Organocatalytic Asymmetric Transformations of 3-Substituted 3-Hydroxyisoindolinones

Abstract

This Account provides an overview of our group’s research in the field of asymmetric organocatalytic transformations generating ­chiral isoindolinone cores. We describe the synthesis of 3-substituted 3-hydroxyisoindolinones as starting materials for these transformations, comprising a wide range of functional groups, as well as their use in asymmetric transformations. We also discuss our efforts in the application of the developed methodology in the synthesis of a known HIV-1 inhibitor.

1 Introduction

2 Synthesis of Isoindolinone Alcohols Comprising Functional Groups

3 Asymmetric Organocatalytic Transformations of Isoindolinone Alcohols

4 Conclusion

Key words

organocatalytic asymmetric transformations - 3-hydroxyisoindolinones - chiral Brønsted acid - isoindolinone core - organometallic addition - chiral N,S-acetals

• References

• 1 Lan Z. Drug Des. Dev. Ther. 2015; 9: 3377
• 2 Suyavaran A, Ramamurthy C, Mareeswaran R, Shanthi YV, Selvakumar J, Mangalaraj S, Kumar MS, Ramanathan CR, Thirunavukkarasu C. Bioorg. Med. Chem. 2015; 23: 488
• 3 Paull KD, Shoemaker RH, Hodes L, Monks A, Scudiero DA, Rubinstein L, Plowman J, Boyd MR. J. Nat. Cancer Inst. 1989; 81: 1088
• 4a Hardcastle IR, Ahmed SU, Atkins H, Calvert AH, Curtin NJ, Farnie G, Golding BT, Griffin RJ, Guyenne S, Hutton C, Källblad P, Kemp SJ, Kitching MS, Newell DR, Norbedo S, Northen JS, Reid RJ, Saravanan K, Willems HM. G, Lunec J. Bioorg. Med. Chem. Lett. 2005; 15: 1515
• 4b Tamayo NA, Bo Y, Gore V, Ma V, Nishimura N, Tang P, Deng H, Klionsky L, Lehto SG, Wang W, Youngblood B, Chen J, Correll TL, Bartberger MD, Gavva NR, Norman MH. J. Med. Chem. 2012; 55: 1593
• 4c Hardcastle IR, Ahmed SU, Atkins H, Farnie G, Golding BT, Griffin RJ, Guyenne S, Hutton C, Källblad P, Kemp SJ, Kitching MS, Newell DR, Norbedo S, Northen JS, Reid RJ, Saravanan K, Willems HM. G, Lunec J. J. Med. Chem. 2006; 49: 6209
• 4d Dempster RK, Luzzio FA. Tetrahedron Lett. 2011; 52: 4992
• 4e Hardcastle IR, Liu J, Valeur E, Watson A, Ahmed SU, Blackburn TJ, Bennaceur K, Clegg W, Drummond C, Endicott JA, Golding BT, Griffin RJ, Gruber J, Haggerty K, Harrington RW, Hutton C, Kemp S, Lu X, McDonnell JM. S, Newell DR, Noble ME. M, Payne SL, Revill CH, Riedinger C, Xu Q, Lunec J. J. Med. Chem. 2011; 54: 1233
• 5 Fardis M, Jin H, Jabri S, Cai RZ, Mish M, Tsiang M, Kim CU. Bioorg. Med. Chem. Lett. 2006; 16: 4031
• 6 Liu DG, Gao Y, Voigt JH, Lee K, Nicklaus MC, Wu L, Zhang ZY, Burke TR. Bioorg. Med. Chem. Lett. 2003; 13: 3005
• 7 Hussein Z, Mulford DJ, Bopp BA, Granneman GR. Br. J. Clin. Pharmacol. 1993; 36: 357
• 8 Carlson JN, Haskew R, Wacker J, Maisonneuve IM, Glick SD, Jerussi TP. Eur. J. Pharmacol. 2001; 415: 181
• 9 Wright J, Reynolds D, Willis G, Edwards M. J. Am. Med. Assoc. 2002; 288: 2981
• 10 Kundu NG, Wahab Khan M, Mukhopadhyay R. Tetrahedron 1999; 55: 12361
• 11 Allin SM, Northfield CJ, Page MI, Slawin AM. Z. Tetrahedron Lett. 1999; 40: 143
• 12 Deniau E, Enders D. Tetrahedron 2001; 57: 2581
• 13 Wang EC, Chen HF, Feng PK, Lin YL, Hsu MK. Tetrahedron Lett. 2002; 43: 9163
• 14 Ruan Y, Chen M, He M, Zhou X, Huang P. Synth. Commun. 2004; 34: 853
• 15 Deglopper KS, Dennis JM, Johnson JB. Tetrahedron Lett. 2014; 55: 1843
• 16a Dennis JM, Calyore CM, Sjoholm JS, Lutz JP, Gair JJ, Johnson JB. Synlett 2013; 24: 2567
• 16b DeGlopper KS, Fodor SK, Endean TB. D, Johnson JB. Polyhedron 2016; 114: 393
• 17 Sharma S, Park E, Park J, Kim IS. Org. Lett. 2012; 14: 906
• 18 Yu Q, Zhang N, Huang J, Lu S, Zhu Y, Yu X, Zhao K. Chem. Eur. J. 2013; 19: 11184
• 19 Li N, Yuan M, Sun Y, Yan H, Wu J, Ma G, Li F, Miao S, Hao M. Heterocycles 2016; 92: 560
• 20 Vacas T, Álvarez E, Chiara JL. Org. Lett. 2007; 9: 5445
• 21 Kise N, Isemoto S, Sakurai T. Tetrahedron 2012; 68: 8805
• 22 Kise N, Kawano Y, Sakurai T. J. Org. Chem. 2013; 78: 12453
• 23 Hatoum F, Engler J, Zelmer C, Wißen J, Motti CA, Lex J, Oelgemöller M. Tetrahedron Lett. 2012; 53: 5573
• 24 Griesbeck AG, Nazarov N, Neudoerfl JM, Heffen M. Green Chem. 2012; 14: 3004
• 25a Chernykh Y, Opekar S, Klepetářová B, Beier P. Synlett 2012; 23: 1187
• 25b Punirun T, Soorukram D, Kuhakarn C, Reutrakul V, Pohmakotr M. Eur. J. Org. Chem. 2014; 4162
• 26 Huang Y.-Y, Cai C, Yang X, Lv Z.-C, Schneider U. ACS Catal. 2016; 6: 5747
• 27a Yu X, Lu A, Wang Y, Wu G, Song H, Zhou Z, Tang C. Eur. J. Org. Chem. 2011; 892
• 27b Yu X, Wang Y, Wu G, Song H, Zhou Z, Tang C. Eur. J. Org. Chem. 2011; 3060
• 28 Aranzamendi E, Sotomayor N, Lete E. J. Org. Chem. 2012; 77: 2986
• 29 Chen M.-W, Chen Q.-A, Duan Y, Ye Z.-S, Zhou Y.-G. Chem. Commun. 2012; 48: 1698
• 30 Zhou JQ, Sheng WJ, Jia JH, Ye Q, Gao JR, Jia YX. Tetrahedron Lett. 2013; 54: 3082
• 31 Nishimura T, Noishiki A, Ebe Y, Hayashi T. Angew. Chem. Int. Ed. 2013; 52: 1777
• 32 Nagamoto M, Yamauchi D, Nishimura T. Chem. Commun. 2016; 52: 5876
• 33 Fodor L, Szabó J, Bernáth G, Sohár P, Maclean DB, Smith RW, Ninomiya I, Naito T. J. Heterocycl. Chem. 1989; 26: 333
• 34 Piller FM, Appukkuttan P, Gavryushin A, Helm M, Knochel P. Angew. Chem. Int. Ed. 2008; 47: 6802
• 35 Leazer JL, Cvetovich R, Tsay FR, Dolling U, Vickery T, Bachert D. J. Org. Chem. 2003; 68: 3695
• 36 Georg GI. Bioorg. Med. Chem. Lett. 1993; 3: 2157
• 37 Usami Y, Aoki S, Numata A. J. Antibiot. 2002; 55: 655
• 38 Mertens A, Zilch H, König B, Schäfer W, Poll T, Kampe W, Seidel H, Leser U, Leinert H. J. Med. Chem. 1993; 36: 2526
• 39 Fang X, Li QH, Tao HY, Wang CJ. Adv. Synth. Catal. 2013; 355: 327
• 40 Wang HY, Zhang JX, Cao DD, Zhao G. ACS Catal. 2013; 3: 2218
• 41 Beceño C, Chauhan P, Rembiak A, Wang A, Enders D. Adv. Synth. Catal. 2015; 357: 672
• 42 Nakamura S, Takahashi S, Nakane D, Masuda H. Org. Lett. 2015; 17: 106
• 43 Ingle GK, Mormino MG, Wojtas L, Antilla JC. Org. Lett. 2011; 13: 4822
• 44 Suć J, Dokli I, Gredičak M. Chem. Commun. 2016; 52: 2071
• 45 Unhale RA, Molleti N, Rana NK, Dhanasekaran S, Bhandary S, Singh VK. Tetrahedron Lett. 2017; 58: 145