Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml
Synthesis 2024; 56(22): 3412-3420
DOI: 10.1055/a-2230-4562
DOI: 10.1055/a-2230-4562
paper
Dual Catalysis
Stereodivergent 1,5-Conjugate Addition with Iminoesters via Pd/Cu Dual Catalysis
We acknowledge the Science and Technology Commission of Shanghai Municipality (22ZR1475200), Natural Science Foundation of Ningbo (2023J036), National Natural Science Foundation of China (NSFC 22071262, 22371292), and Shanghai Institute of Organic Chemistry for financial support.
Abstract
The first stereodivergent umpolung 1,5-conjugate addition reaction via synergistic Pd/Cu catalysts is reported. By dictating the absolute configuration of each chiral ligand ligated to corresponding metals, all four stereoisomers of the products are easily achieved. A series of amino acid moieties are introduced to the γ-position of the conjugated esters in high yields with excellent diastereoselectivities and enantioselectivities. The downstream transformations highlight the synthetic value of the method.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-2230-4562.
- Supporting Information
Publication History
Received: 25 November 2023
Accepted after revision: 15 December 2023
Accepted Manuscript online:
15 December 2023
Article published online:
19 January 2024
© 2024. Thieme. All rights reserved
Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany
-
References
- 1 Csaky AG, Herran GD. L, Murcia MC. Chem. Soc. Rev. 2010; 39: 4080
- 2 Chauhan P, Kaya U, Enders D. Adv. Synth. Catal. 2017; 359: 888
- 3 Hussain Y, Tamanna Tamanna, Sharma M, Kumar A, Chauhan P. Org. Chem. Front. 2022; 9: 572
- 4a Tian X, Liu Y, Melchiorre P. Angew. Chem. Int. Ed. 2012; 51: 6439
- 4b Luo Y, Roy ID, Madec AG. E, Lam HW. Angew. Chem. Int. Ed. 2014; 53: 4186
- 4c Lu J, Ye J, Duan W.-L. Chem. Commun. 2014; 50: 698
- 4d Wang M, Liu Z.-L, Zhang X, Tian P.-P, Xu Y.-H, Loh T.-P. J. Am. Chem. Soc. 2015; 137: 14830
- 4e Shaw S, White JD. Org. Lett. 2015; 17: 4564
- 4f Dong N, Zhang Z.-P, Xue X.-S, Li X, Cheng J.-P. Angew. Chem. Int. Ed. 2016; 55: 1460
- 4g Poulsen PH, Vergura S, Monleon A, Jorgensen DK. B, Jorgensen KA. J. Am. Chem. Soc. 2016; 138: 6412
- 4h Dou Q.-Y, Tu Y.-Q, Zhang Y, Tian J.-M, Zhang F.-M, Wang S.-H. Adv. Synth. Catal. 2016; 358: 874
- 4i Wei X, Lu J, Duan W.-L. Synthesis 2016; 48: 4155
- 4j Shi CY, Eun J, Newhouse TR, Yin L. Angew. Chem. Int. Ed. 2021; 60: 9493
- 5 Wang Y.-C, Xiao Z.-X, Wang M, Yang S.-Q, Liu J.-B, He Z.-T. Angew. Chem. Int. Ed. 2023; 62: e202215568
- 6 Liao Q.-Y, Ma C, Wang Y.-C, Yang S.-Q, Ma J.-S, He Z.-T. Chin. Chem. Lett. 2023; 34: 108371
- 7 Krautwald S, Sarlah D, Schafroth MA, Carreira EM. Science 2013; 340: 1065
- 8a Krautwald S, Carreira EM. J. Am. Chem. Soc. 2017; 139: 5627
- 8b Kalita SJ, Huang Y.-Y, Schneider U. Sci. Bull. 2020; 65: 1865
- 8c Huo X, Li G, Wang X, Zhang W. Angew. Chem. Int. Ed. 2022; 61: e202210086
- 9a Krautwald S, Schafroth MA, Sarlah D, Carreira EM. J. Am. Chem. Soc. 2014; 136: 3020
- 9b Næsborg L, Halskov KS, Tur F, Mønsted SM. N, Jørgensen KA. Angew. Chem. Int. Ed. 2015; 54: 10193
- 9c Huo X, He R, Zhang X, Zhang W. J. Am. Chem. Soc. 2016; 138: 11093
- 9d Jiang X, Beiger JJ, Hartwig JF. J. Am. Chem. Soc. 2017; 139: 87
- 9e Cruz FA, Dong VM. J. Am. Chem. Soc. 2017; 139: 1029
- 9f Huo X, He R, Fu J, Zhang J, Yang G, Zhang W. J. Am. Chem. Soc. 2017; 139: 9819
- 9g Wei L, Zhu Q, Xu S.-M, Chang X, Wang C.-J. J. Am. Chem. Soc. 2018; 140: 1508
- 9h Huo X, Zhang J, Fu J, He R, Zhang W. J. Am. Chem. Soc. 2018; 140: 2080
- 9i He Z.-T, Jiang X, Hartwig JF. J. Am. Chem. Soc. 2019; 141: 13066
- 9j Zhang Q, Yu H, Shen L, Tang T, Dong D, Chai W, Zi W. J. Am. Chem. Soc. 2019; 141: 14554
- 9k Singha S, Serrano E, Mondal S, Daniliuc CG, Glorius F. Nat. Catal. 2020; 3: 48
- 9l He R, Huo X, Zhao L, Wang F, Jiang L, Liao J, Zhang W. J. Am. Chem. Soc. 2020; 142: 8097
- 9m Yang S.-Q, Wang Y.-F, Zhao W.-C, Lin G.-Q, He Z.-T. J. Am. Chem. Soc. 2021; 143: 7285
- 9n Zhu M, Zhang Q, Zi W. Angew. Chem. Int. Ed. 2021; 60: 6545
- 9o Wen YH, Zhang ZJ, Li S, Song J, Gong LZ. Nat. Commun. 2022; 13: 1344
- 9p He Z, Peng L, Guo C. Nat. Synth. 2022; 1: 393
- 9q Le TP, Tanaka S, Yoshimura M, Sato K, Kitamura M. Nat. Commun. 2022; 13: 5876
- 9r Chang X, Cheng X, Liu X.-T, Fu C, Wang W.-Y, Wang C.-J. Angew. Chem. Int. Ed. 2022; 61: e202206517
- 9s Zhao L, Luo Y, Xiao J, Huo X, Ma S, Zhang W. Angew. Chem. Int. Ed. 2023; 62: e202218146
- 10a Kim B, Kim Y, Lee SY. J. Am. Chem. Soc. 2021; 143: 73
- 10b Kim S, Jeung S, Lee SY. ACS Catal. 2023; 13: 13838
- 11a Li G, Huo X, Jiang X, Zhang W. Chem. Soc. Rev. 2020; 49: 2060
- 11b Adamson NJ, Malcolmson SJ. ACS Catal. 2020; 10: 1060
- 11c Ma C, Chen Y.-W, He Z.-T. Sci. Sin. Chim. 2023; 53: 474
- 11d Wang Y.-C, Liu J.-B, He Z.-T. Chin. J. Org. Chem. 2023; 43: 2614
- 12a Chen Y.-W, Liu Y, Lu H.-Y, Lin G.-Q, He Z.-T. Nat. Commun. 2021; 12: 5626
- 12b Yang S.-Q, Han A.-J, Liu Y, Tang X.-Y, Lin G.-Q, He Z.-T. J. Am. Chem. Soc. 2023; 145: 3915
- 12c Miao H.-Z, Liu Y, Chen Y.-W, Lu H.-Y, Li J, Lin G.-Q, He Z.-T. Synlett 2023; 34: 451
- 12d Wang X, Miao H.-Z, Lin G.-Q, He Z.-T. Angew. Chem. Int. Ed. 2023; 62: e202301556
- 12e Tang M, Yang Z.-J, He Z.-T. Nat. Commun. 2023; 14: 6303
- 12f Chen X.-X, Luo H, Chen Y.-W, Liu Y, He Z.-T. Angew. Chem. Int. Ed. 2023; 62: e202307628
For selected work, see:
For reviews and perspectives, see:
For selected work, see:
For reviews, see: