Photoinduced Stereoselective Giese Addition on Coumarins

Abstract

Diastereoselective Giese addition on coumarin-3-carboxylate bearing a chiral auxiliary with N-hydroxyphthalimide ester to generate the corresponding alkylated adduct has been explored. Among screened chiral auxiliaries, bulkier one with appropriate steric hindrance is better for diastereoselective addition. Mechanistic studies involving fluorescence studies and On/Off experiments shed insight onto the plausible reaction pathway.

Key words

diastereoselectivity - coumarin-3-carboxylate - (+)-phenylmenthol - N-hydroxyphthalimide ester - Eosin Y

• References

• 1a Zhang N, Samanta SR, Rosen BM, Percec V. Chem. Rev. 2014; 114: 5848
• 1b Studer A, Curran DP. Angew. Chem. Int. Ed. 2016; 55: 58
• 1c Sumida Y, Ohmiya H. Chem. Soc. Rev. 2021; 50: 6320
• 1d Bell JD, Murphy JA. Chem. Soc. Rev. 2021; 50: 9540
• 1e Reischauer S, Pieber B. iScience 2021; 24: 102209
• 2a Inoue Y. Chem. Rev. 1992; 92: 741
• 2b Svoboda J, König B. Chem. Rev. 2006; 106: 5413
• 3a Nicewicz DA, MacMillan DW. C. Science 2008; 322: 77
• 3b Shih H.-W, Vander Wal MN, Grange RL, MacMillan DW. C. J. Am. Chem. Soc. 2010; 132: 13600
• 3c DiRocco DA, Rovis T. J. Am. Chem. Soc. 2012; 134: 8094
• 3d Huo H, Harms K, Meggers E. J. Am. Chem. Soc. 2016; 138: 6936
• 4a Silvestri IP, Colbon PJ. J. ACS Med. Chem. Lett. 2021; 12: 1220
• 4b McVicker RU, O’Boyle NM. J. Med. Chem. 2024; 67: 2305
• 5a Yeom J. Acc. Mater. Res. 2021; 2: 471
• 5b Meskers SC. J. Mater. Adv. 2022; 3: 2324
• 6 Bauer A, Westkämper F, Grimme S, Bach T. Nature 2005; 436: 1139
• 7 Ruiz Espelt L, McPherson IS, Wiensch EM, Yoon TP. J. Am. Chem. Soc. 2015; 137: 2452
• 8 Lahdenperä AS. K, Bacoş PD, Phipps RJ. J. Am. Chem. Soc. 2022; 144: 22451
• 9 Gentry EC, Rono LJ, Hale ME, Matsuura R, Knowles RR. J. Am. Chem. Soc. 2018; 140: 3394
• 10 Liang K, Tong X, Li T, Shi B, Wang H, Yan P, Xia C. J. Org. Chem. 2018; 83: 10948
• 11 Zhang Y, Ji P, Gao F, Huang H, Zeng F, Wang W. ACS Catal. 2021; 11: 998
• 12 Leone M, Milton JP, Gryko D, Neuville L, Masson G. Chem. Eur. J. 2024; 30: e202400363
• 13 Yu F, Dickson JL, Loka RS, Xu H, Schaugaard RN, Schlegel HB, Luo L, Nguyen HM. ACS Catal. 2020; 10: 5990
• 14a Sun AC, McClain EJ, Beatty JW, Stephenson CR. J. Org. Lett. 2018; 20: 3487
• 14b Tripathi KN, Belal Md, Singh RP. J. Org. Chem. 2020; 85: 1193
• 14c Singh S, Tripathi KN, Singh RP. Org. Biomol. Chem. 2022; 20: 5716
• 15a Tada M, Okuno K, Chiba K, Ohnishi E, Yoshii T. Phytochemistry 1994; 35: 539
• 15b Zhang X, Wang H, Song Y, Nie L, Wang L, Liu B, Shen P, Liu Y. Bioorg. Med. Chem. Lett. 2006; 16: 949
• 15c Lv H.-N, Wang S, Zeng K.-W, Li J, Guo X.-Y, Ferreira D, Zjawiony JK, Tu P.-F, Jiang Y. J. Nat. Prod. 2015; 78: 279
• 15d Singh LR, Avula SR, Raj S, Srivastava A, Palnati GR, Tripathi CK. M, Pasupuleti M, Sashidhara KV. J. Antibiot. 2017; 70: 954