Chiral Phosphoric Acid Catalyzed Cascade Asymmetric Allylboration/Oxa-Cyclization of Aldehydes for Access to Multisubstituted Tetrahydrofurans

Zihan Li; Yichao Li; Ruihao Zhang; Yuhao Wang; Yilong Wang; Ziqi Yi; Yiyong Huang

doi:10.1055/a-2513-1926

Synthesis, Table of Contents

Synthesis 2025; 57(15): 2307-2319
DOI: 10.1055/a-2513-1926

feature

Chiral Phosphoric Acid Catalyzed Cascade Asymmetric Allylboration/Oxa-Cyclization of Aldehydes for Access to Multisubstituted Tetrahydrofurans

Authors

Zihan Li‡

^aDepartment of Chemistry, School of Chemistry, Chemical Engineering, and Life Science, Wuhan University of Technology, Wuhan 430070, P. R. of China
Yichao Li‡

^aDepartment of Chemistry, School of Chemistry, Chemical Engineering, and Life Science, Wuhan University of Technology, Wuhan 430070, P. R. of China
Ruihao Zhang

^aDepartment of Chemistry, School of Chemistry, Chemical Engineering, and Life Science, Wuhan University of Technology, Wuhan 430070, P. R. of China
Yuhao Wang

^aDepartment of Chemistry, School of Chemistry, Chemical Engineering, and Life Science, Wuhan University of Technology, Wuhan 430070, P. R. of China
Yilong Wang

^aDepartment of Chemistry, School of Chemistry, Chemical Engineering, and Life Science, Wuhan University of Technology, Wuhan 430070, P. R. of China
Ziqi Yi∗

^bSchool of Chemistry and Chemical Engineering, Shanghai University of Engineering Science, Shanghai 201210, P. R. of China
Yiyong Huang∗

^aDepartment of Chemistry, School of Chemistry, Chemical Engineering, and Life Science, Wuhan University of Technology, Wuhan 430070, P. R. of China

Abstract

All articles of this category

Abstract

Optically pure homoallylic alcohols, important synthons for natural products and bioactive compounds, can be assembled by a chiral phosphoric acid catalyzed asymmetric allylboration of aldehydes. Based on this reaction, two unprecedented cascade reactions of functionalized aldehydes (allylation/oxa-Michael or oxa-Pictet–Spengler reactions) for the synthesis of chiral 2,5-disubstituted and 2,2,5-trisubstituted tetrahydrofurans using a single chiral phosphoric acid catalyst have been developed. The reaction mechanism proposed here of the oxa-Pictet–Spengler reaction was investigated through control experiments.

Key words

substituted tetrahydrofurans - chiral phosphoric acid - cascade reaction - allylboration - oxa-cyclization

Full Text

References

References
1 Yus M, González-Gómez JC, Foubelo F. Chem. Rev. 2011; 111: 7774
2 Ortiz E, Saludares C, Wu J, Cho Y, Santana CG, Krische MJ. Synthesis 2023; 55: 1487

3a Jain P, Antilla JC. J. Am. Chem. Soc. 2010; 132: 11884
3b Barrio P, Rodríguez E, Saito K, Fustero S, Akiyama T. Chem. Commun. 2015; 51: 5246
3c Ota Y, Kawato Y, Egami H, Hamashima Y. Synlett 2017; 28: 976
3d Gao S, Duan M, Houk KN, Chen M. Angew. Chem. Int. Ed. 2020; 59: 10540
3e Yuan J, Jain P, Antilla JC. J. Org. Chem. 2020; 85: 12988
3f Gao S, Liu J, Chen M. Chem. Sci. 2021; 12: 13398
3g Gao S, Duan M, Andreola LR, Yu P, Wheeler SE, Houk KN, Chen M. Angew. Chem. Int. Ed. 2022; 61: e202208908
3h Zhang Z, Chen M. Org. Lett. 2024; 26: 10102

4a Huang Y, Yang X, Lv Z, Cai C, Kai C, Pei Y, Feng Y. Angew. Chem. Int. Ed. 2015; 54: 7299
4b Zhang Y, He B, Xie Y, Wang Y, Wang Y, Shen Y, Huang Y. Adv. Synth. Catal. 2019; 361: 3074
4c Zhang Y, Zhao Z, Li W, Li J, Kalita SJ, Schneider U, Huang Y. Chem. Commun. 2020; 56: 10030
4d Kalita SJ, Cheng F, Huang Y. Adv. Synth. Catal. 2020; 362: 2778
4e Yang X, Pang S, Cheng F, Zhang Y, Lin Y, Yuan Q, Zhang F, Huang Y. J. Org. Chem. 2017; 82: 10388

5a Pereira CL, Chen Y, McDonald FE. J. Am. Chem. Soc. 2009; 131: 6066
5b Lu Z, Zhang X, Guo Z, Chen Y, Mu T, Li A. J. Am. Chem. Soc. 2018; 140: 9211
5c Yus M, González-Gómez JC, Foubelo F. Chem. Rev. 2013; 113: 5595

6 Yang X, Kalita SJ, Maheshuni S, Huang Y. Coord. Chem. Rev. 2019; 392: 35
7 Fustero S, Rodríguez E, Lázaro R, Herrera L, Catalán S, Barrio P. Adv. Synth. Catal. 2013; 355: 1058
8 Calder ED. D, Sutherland A. Org. Lett. 2015; 17: 2514
9 Miura T, Nakahashi J, Zhou W, Shiratori Y, Stewart SG, Murakami M. J. Am. Chem. Soc. 2017; 139: 10903
10 Loiseau F, Kholod I, Neier R. Eur. J. Org. Chem. 2010; 4642
11 Rasina D, Otikovs M, Leitans J, Recacha R, Borysov OV, Kanepe-Lapsa I, Domraceva I, Pantelejevs T, Tars K, Blackman MJ, Jaudzems K, Jirgensons A. J. Med. Chem. 2016; 59: 374
12 Brooks JL, Xu L, Wiest O, Tan DS. J. Org. Chem. 2017; 82: 57
13 Volz F, Krause N. Org. Biomol. Chem. 2007; 5: 1519

14a Čorić I, Vellalath S, List B. J. Am. Chem. Soc. 2010; 132: 8536
14b Das S, Liu L, Zheng Y, Alachraf MW, Thiel W, De CK, List B. J. Am. Chem. Soc. 2016; 138: 9429

15 Zhang Y.-C, Jiang F, Shi F. Acc. Chem. Res. 2020; 53: 425

16a Gtsyson MN, Pellegrinet SC, Goodman JM. J. Am. Chem. Soc. 2012; 134: 2716
16b Grayson MN, Yang Z, Houk KN. J. Am. Chem. Soc. 2017; 139: 7717

17 Luo W, Sun Z, Fernando EH. N, Nesterov VN, Cundari TR, Wang H. Chem. Sci. 2020; 11: 9386

Supplementary Material

Supporting Information (PDF)