Photoredox-Mediated Asymmetric Cross-Dehydrogenative Coupling of Enones and Tertiary Amines by Chiral Primary Amine Catalysis

Abstract

A catalytic asymmetric dehydrogenative cross-coupling reaction between enones and tertiary amines enabled by synergistic photoredox and chiral primary amine catalysis is reported. The reaction was proposed to proceed via the interception of iminium ion intermediate, in situ generated from photoredox oxidation, by dienamine at α-position, followed by isomerization, leading to aza-Morita–Baylis–Hillman-type products with good diastereo- and enantioselectivity.

Key words

cross dehydrogenative coupling - photoredox oxidation - primary amine catalysis - dienamine - enone

Publication History

Received: 21 February 2021

Accepted after revision: 24 March 2021

Accepted Manuscript online:
24 March 2021

Article published online:
19 April 2021

• References


For selected reviews, see:
• 1a Parvatkar PT, Manetsch R, Banik BK. Chem. Asian J. 2019; 14: 6
• 1b Chen B, Wu L.-Z, Tung C.-H. Acc. Chem. Res. 2018; 51: 2512
• 1c Yang Y, Lan J, You J. Chem. Rev. 2017; 117: 8787
• 1d Liu C, Yuan J, Gao M, Tang S, Li W, Shi R, Lei A. Chem. Rev. 2015; 115: 12138
• 1e Girard SA, Knauber T, Li C.-J. Angew. Chem. Int. Ed. 2014; 53: 74
• 1f Tang C, Jiao N. Chem. Soc. Rev. 2012; 41: 3381
• 1g Yeung CS, Dong VM. Chem. Rev. 2011; 111: 1215

For selected reviews on C–H olefinations, see:
• 2a Rej S, Ano Y, Naoto C. Chem. Rev. 2020; 120: 1788
• 2b Hu Y, Wang C. ChemCatChem 2019; 11: 1167
• 2c Wang C.-S, Dixneuf PH, Soulé J.-F. Chem. Rev. 2018; 118: 7532
• 2d Wei Y, Hu P, Zhang M, Su W. Chem. Rev. 2017; 117: 8864
• 2e Manikandan R, Jeganmohan M. Chem. Commun. 2017; 53: 8931
• 3a Li Z, Bohle DS, Li C.-J. Proc. Natl. Acad. Sci. U.S.A. 2006; 103: 8928
• 3b Zhang G, Ma Y, Wang S, Zhang Y, Wang R. J. Am. Chem. Soc. 2012; 134: 12334
• 3c Ma Y, Zhang G, Zhang J, Yang D, Wang R. Org. Lett. 2014; 16: 5358
• 3d Feng Z.-J, Xuan J, Xia X.-D, Ding W, Guo W, Chen J.-R, Zou Y.-Q, Lu L.-Q, Xiao W.-J. Org. Biomol. Chem. 2014; 12: 2037
• 3e Wei G, Zhang C, Bureš F, Ye X, Tan C.-H, Jiang Z. ACS Catal. 2016; 6: 3708

For reviews about dienamine catalysis, see:
• 4a Curti C, Battistini L, Sartori A, Zanardi F. Chem. Rev. 2020; 120: 2448
• 4b Marcos V, Alemán J. Chem. Soc. Rev. 2016; 45: 6812
• 4c Jurberg ID, Chatterjee I, Tannert R, Melchiorre P. Chem. Commun. 2013; 49: 4869
• 5 For CDC reactions of carbonyl compounds with tertiary amines, see: Rostoll-Berenguer J, Blay G, Pedro JR, Vila C. Adv. Synth. Catal. 2021; 363: 602

For selected cycloaddition reactions of cyclic 2-enones in recent years, see:
• 6a Zhou Z, Wang Z.-X, Zhou Y.-C, Xiao W, Ouyang Q, Du W, Chen Y.-C. Nat. Chem. 2017; 9: 590
• 6b Mose R, Preegel G, Larsen J, Jakobsen S, Iversen EH, Jørgensen KA. Nat. Chem. 2017; 9: 487
• 6c Zou C, Zeng C, Liu Z, Lu M, Sun X, Ye J. Angew. Chem. Int. Ed. 2016; 55: 14257
• 6d Mose R, Jensen ME, Preegel G, Jørgensen KA. Angew. Chem. Int. Ed. 2015; 54: 13630
• 6e Yin X, Zheng Y, Feng X, Jiang K, Wei X.-Z, Gao N, Chen Y.-C. Angew. Chem. Int. Ed. 2014; 53: 6245
• 6f Han B, He Z.-Q, Li J.-L, Li R, Jiang K, Liu T.-Y, Chen Y.-C. Angew. Chem. Int. Ed. 2009; 48: 5474
• 6g Li M.-M, Xiong Q, Qu B.-L, Xiao Y.-Q, Lan Y, Lu L.-Q, Xiao W.-J. Angew. Chem. Int. Ed. 2020; 59: 17429
• 7a Sofiadis M, Kalaitzakis D, Sarris J, Montagnon T, Vassilikogiannakis G. Angew. Chem. Int. Ed. 2019; 58: 6742
• 7b Huang Y.-S, Song S.-G, Ren L, Li Y.-G, Wu X. Eur. J. Org. Chem. 2019; 6838
• 7c Iorio ND, Righi P, Mazzanti A, Mancinelli M, Ciogli A, Bencivenni G. J. Am. Chem. Soc. 2014; 136: 10250
• 7d Zhan G, He Q, Yuan X, Chen Y.-C. Org. Lett. 2014; 16: 6000
• 7e Bastida D, Liu Y, Tian X, Escudero-Adán E, Melchiorre P. Org. Lett. 2013; 15: 220
• 7f Bencivenni G, Galzerano P, Mazzanti A, Bartoli G, Melchiorre P. Proc. Natl. Acad. Sci. U. S. A. 2010; 107: 20642

For α-additions of dienamine, see:
• 8a Kutwal MS, Padmaja VM. D, Appayee C. Eur. J. Org. Chem. 2020; 2720
• 8b Maity S, Sar S, Ghorai P. Org. Lett. 2018; 20: 1707
• 8c Arimitsu S, Yonamine T, Higashi M. ACS Catal. 2017; 7: 4736
• 8d Stiller J, Marqués-López E, Herrera RP, Fröhlich R, Strohmann C, Christmann M. Org. Lett. 2011; 13: 70
• 8e Číhalová S, Dziedzic P, Córdova A, Veselý J. Adv. Synth. Catal. 2011; 353: 1096
• 8f Han B, Xiao Y.-C, He Z.-Q, Chen Y.-C. Org. Lett. 2009; 11: 4660
• 8g Marqués-López E, Herrera RP, Marks T, Jacobs WC, Könning D, Figueiredo RM, Christmann M. Org. Lett. 2009; 11: 4116
• 8h Vesely J, Dziedzic P, Córdova A. Tetrahedron Lett. 2007; 48: 6900
• 8i Utsumi N, Zhang H, Tanaka F, Barbas CF. Angew. Chem. Int. Ed. 2007; 46: 1878
• 9a Jia Z, Yang Q, Zhang L, Luo S. ACS Catal. 2019; 9: 3589
• 9b Zhu L, Wang D, Jia Z, Lin Q, Huang M, Luo S. ACS Catal. 2018; 8: 5466
• 9c Zhang W, Zhu Y, Zhang L, Luo S. Chin. J. Chem. 2018; 36: 716
• 9d Yang Q, Jia Z, Li L, Zhang L, Luo S. Org. Chem. Front. 2018; 5: 237
• 9e Yang Q, Zhang L, Ye C, Luo S, Wu L.-Z, Tung C.-H. Angew. Chem. Int. Ed. 2017; 56: 3694
• 9f Wang D, Zhang L, Luo S. Org. Lett. 2017; 19: 4924
• 9g Zhang L, Fu N, Luo S. Acc. Chem. Res. 2015; 48: 986
• 9h Zhu Y, Zhang L, Luo S. J. Am. Chem. Soc. 2014; 136: 14642
• 10a Xu G.-Q, Xu J.-T, Feng Z.-T, Liang H, Wang Z.-Y, Qin Y, Xu P.-F. Angew. Chem. Int. Ed. 2018; 57: 5110
• 10b Chen H.-W, Lu F.-D, Cheng Y, Jia Y, Lu L.-Q, Xiao W.-J. Chin. J. Chem. 2020; 38: 1671
• 11 Acid additive m-NO₂C₆H₄CO₂H as hydrogen acceptor could not be excluded, see Table 1, entry 11 and ref. 9e.
• 12 Wang Y, Zhou H, Yang K, You C, Zhang L, Luo S. Org. Lett. 2019; 21: 407
• 13a Zhang T, Liang W, Huang Y, Li X, Liu Y, Yang B, He C, Zhou X, Zhang J. Chem. Commun. 2017; 53: 12536
• 13b Xia Q, Tian H, Dong J, Qu Y, Li L, Song H, Liu Y, Wang Q. Chem. Eur. J. 2018; 24: 9269
• 13c Barraza SJ, Denmark SE. J. Am. Chem. Soc. 2018; 140: 6668
• 13d Lockhart Z, Knipe PC. Angew. Chem. Int. Ed. 2018; 57: 8478
• 13e Yu F, Hu H, Gu X, Ye J. Org. Lett. 2012; 14: 2038
• 13f Misaki T, Takimoto G, Sugimura T. J. Am. Chem. Soc. 2010; 132: 6286