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

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

› Author Affiliations

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