Stereodivergent 1,5-Conjugate Addition with Iminoesters via Pd/Cu Dual Catalysis

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.

Key words

stereodivergent - 1,5-conjugate addition - palladium - copper - synergistic catalysis

Publikationsverlauf

Eingereicht: 25. November 2023

Angenommen nach Revision: 15. Dezember 2023

Accepted Manuscript online:
15. Dezember 2023

Artikel online veröffentlicht:
19. Januar 2024

• 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

For selected work, see:
• 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

For reviews and perspectives, see:
• 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

For selected work, see:
• 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

For reviews, see:
• 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 reviews, see:
• 13a Wu Y, Huo X, Zhang W. Chem. Eur. J. 2020; 26: 4895
• 13b Kim UB, Jung DJ, Jeon HJ, Rathwell K, Lee S.-g. Chem. Rev. 2020; 120: 13382