Rhodium(III)-Catalyzed Enantioselective Benzamidation of Cyclopropenes

Saad Shaaban; Houhua Li; Christian Merten; Andrey P. Antonchick; Herbert Waldmann

doi:10.1055/s-0040-1706026

Synthesis, Table of Contents

Synthesis 2021; 53(13): 2192-2200
DOI: 10.1055/s-0040-1706026

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Rhodium(III)-Catalyzed Enantioselective Benzamidation of Cyclopropenes

Saad Shaaban

^aMax Planck Institute of Molecular Physiology, Otto-Hahn Straße 11, 44227 Dortmund, Germany

,

Houhua Li

^aMax Planck Institute of Molecular Physiology, Otto-Hahn Straße 11, 44227 Dortmund, Germany

,

Christian Merten

^bOrganic Chemistry II, Ruhr University Bochum, Universitätsstraße 150, 44801 Bochum, Germany

,

Andrey P. Antonchick ∗

^aMax Planck Institute of Molecular Physiology, Otto-Hahn Straße 11, 44227 Dortmund, Germany

^cDepartment of Chemical Biology, Technical University Dortmund, Otto-Hahn Straße 4a, 44227 Dortmund, Germany

^dDepartment of Chemistry and Forensics, College of Science and Technology, Nottingham Trent University, Clifton Lane, Nottingham, NG11 8NS, UK

,

Herbert Waldmann ∗

^aMax Planck Institute of Molecular Physiology, Otto-Hahn Straße 11, 44227 Dortmund, Germany

^cDepartment of Chemical Biology, Technical University Dortmund, Otto-Hahn Straße 4a, 44227 Dortmund, Germany

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Abstract

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Abstract

Cyclopropylamines are characteristic structural motifs found in a variety of natural products and pharmaceuticals and therefore engaging targets for the development of new methods for their synthesis. Herein the synthesis of enantioenriched cyclopropylamines through catalytic enantioselective C–H functionalization using a chiral RhJasCp complex is reported. The reaction proceeds under mild conditions with high enantiocontrol. This reaction enables access to cyclopropylamines with three contiguous stereocenters originating from the corresponding cyclopropenes.

Key words

rhodium catalysis - cyclopropenes - chiral cyclopentadiene - C–H activation - cyclopropylamine

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References

References

1a de Meijere A. Angew. Chem., Int. Ed. Engl. 1979; 18: 809
1b Bach RD, Dmitrenko O. J. Org. Chem. 2002; 67: 2588

2a Donaldson WA. Tetrahedron 2001; 57: 8589
2b Taylor RD, MacCoss M, Lawson AD. J. Med. Chem. 2014; 57: 5845

3a Talele TT. J. Med. Chem. 2016; 59: 8712
3b Časar Z. Synthesis 2020; 52: 1315

For selected reviews, see:

4a Salaün J. Chem. Rev. 1989; 89: 1247
4b Reissig H.-U. Angew. Chem. Int. Ed. 1996; 35: 971
4c Lebel H, Marcoux J.-F, Molinaro C, Charette AB. Chem. Rev. 2003; 103: 977
4d Chen Y.-KD, Pouwer RH, Richard J.-A. Chem. Soc. Rev. 2012; 41: 4631
4e Dian L, Marek I. Chem. Rev. 2018; 118: 8415
4f Mato M, Franchino A, Garcıá-Morales C, Echavarren AM. Chem. Rev. 2020; in press;

For selected examples, see:

5a Furukawa J, Kawabata N, Nishimura J. Tetrahedron Lett. 1966; 7: 3353
5b Mamane V, Gress T, Krause H, Fürstner A. J. Am. Chem. Soc. 2004; 126: 8654
5c Johansson MJ, Gorin DJ, Staben ST, Toste D. J. Am. Chem. Soc. 2005; 127: 18002
5d Riches SL, Chandreyee Saha C, Filgueira NF, Grange E, McGarrigle EM, Aggarwal VK. J. Am. Chem. Soc. 2010; 132: 7626
5e Terrasson V, van der Lee A, de Figueiredo RM, Campagne JM. Chem. Eur. J. 2010; 16: 7875
5f Lindsay VN. G, Fiset D, Gritsch PJ, Azzi S, Charette AB. J. Am. Chem. Soc. 2013; 135: 1463
5g Sabbatani J, Huang X, Veiros LF, Maulide N. Chem. Eur. J. 2014; 20: 10636
5h Lauterbach T, Ganschow M, Hussong MW, Rudolph M, Rominger F, Hashmi AS. K. Adv. Synth. Catal. 2014; 356: 680
5i Klimczyk S, Misale A, Huang X, Maulide N. Angew. Chem. Int. Ed. 2015; 54: 10365
5j del Hoyo AM, Suero MG. Eur. J. Org. Chem. 2017; 2122
5k Ernouf G, Brayer J.-L, Folléas F, Demoute J.-P, Meyer C, Cossy J. J. Org. Chem. 2017; 82: 3965
5l Peil S, Guthertz A, Biberger T, Fürstner A. Angew. Chem. Int. Ed. 2019; 58: 8851
5m Phipps EJ. T, Rovis T. J. Am. Chem. Soc. 2019; 141: 6807
5n Xu B, Troian-Gautier L, Dykstra R, Martin RT, Gutierrez O, Tambar UK. J. Am. Chem. Soc. 2020; 142: 6206

6 Khan MN. A, Suzuki T, Miyata N. Med. Res. Rev. 2013; 33: 873

7a Miller JA, Hennessy EJ, Marshall WJ, Scialdone MA, Nguyen ST. J. Org. Chem. 2003; 68: 7884
7b Armstrong A, Scutt JN. Chem. Commun. 2004; 510
7c Yoshida K, Yamaguchi K, Mizuno A, Unno Y, Asai A, Sone T, Yokosawa H, Matsuda A, Arisawa M, Shuto S. Org. Biomol. Chem. 2009; 7: 1868

8a Gu P, Su Y, Wu X.-P, Sun J, Liu W, Xue P, Li R. Org. Lett. 2012; 14, 2246
8b Sambasivan R, Ball ZT. Angew. Chem. Int. Ed. 2012; 51: 8568
8c Chanthamath S, Nguyen DT, Shibatomi K, Iwasa S. Org. Lett. 2013; 15: 772
8d Huang K.-X, Xie M.-S, Zhao G.-F, Qu G.-R, Guo H.-M. Adv. Synth. Catal. 2016; 358: 3627
8e Brandenberg OF, Prier CK, Chen K, Knight AM, Wu Z, Arnold FH. ACS Catal. 2018; 8: 2629
8f Shao X, Malcolmson SJ. Org. Lett. 2019; 21: 7380

9a Pedroni J, Cramer N. Angew. Chem. Int. Ed. 2015; 54: 11826
9b Pedroni J, Saget T, Donets PA, Cramer N. Chem. Sci. 2015; 6: 5164
9c Mayer C, Ladd CL, Charette AB. Org. Lett. 2019; 21: 2639

For selected reviews on the reactivity of cyclopropenes, see:

10a Rubin M, Rubina M, Gevorgyan V. Synthesis 2006; 8: 1221
10b Zhu ZB, Wei Y, Shi M. Chem. Soc. Rev. 2011; 40: 5534
10c Li P, Zhang X, Shi M. Chem. Commun. 2020; 56: 5457
10d Raiguru BP, Nayak S, Mishra DR, Das T, Mohapatra S, Mishra NP. Asian J. Org. Chem. 2020; 9: 1088
10e Vicente R. Chem. Rev. 2020; in press;

11a Parra A, Amenls L, Guisan-Ceinos M, Lopez A, Ruano JL. G, Tortosa M. J. Am. Chem. Soc. 2014; 136: 15833
11b Teng H.-L, Luo Y, Wang B, Zhang L, Nishiura M, Hou Z. Angew. Chem. Int. Ed. 2016; 55: 15406
11c Teng H.-L, Luo Y, Nishiura M, Hou Z. J. Am. Chem. Soc. 2017; 139: 16506
11d Li Z, Zhao J, Sun B, Zhou T, Liu M, Liu S, Zhang M, Zhang Q. J. Am. Chem. Soc. 2017; 139: 11702
11e Simaan M, Marek I. Angew. Chem. Int. Ed. 2018; 57: 1543
11f Li Z, Zhang M, Zhang Y, Liu S, Zhao J, Zhang Q. Org. Lett. 2019; 21: 5432
11g Feng S, Hao H, Liu P, Buchwald SL. ACS Catal. 2020; 10: 282
11h Zhang Y, Li Y, Zhou W, Zhang M, Zhang Q, Jia R, Zhao J. Chem. Commun. 2020; 56: 12250

For recent reviews on chiral cyclopentadiene–metal complexes, see:

12a Shaaban S, Davies C, Waldmann H. Eur. J. Org. Chem. 2020; 6512
12b Mas-Rosello J, Herraiz AG, Audic B, Laverny A, Cramer N. Angew. Chem. Int. Ed. 2020; 59 in press;

For the synthesized chiral cyclopentadiene ligands, see:

13a Gutnov A, Heller B, Fischer C, Drexler H.-J, Spannenberg A, Sundermann B, Sundermann C. Angew. Chem. Int. Ed. 2004; 43: 3795
13b Hyster TK, Knörr L, Ward TR, Rovis T. Science 2012; 338: 500
13c Ye B, Cramer N. Science 2012; 338: 504
13d Ye B, Cramer N. J. Am. Chem. Soc. 2013; 135: 636
13e Zheng J, Cui W.-J, Zheng C, You S.-L. J. Am. Chem. Soc. 2016; 138: 5242
13f Jia Z.-J, Merten C, Gontla R, Daniliuc CG, Antonchick AP, Waldmann H. Angew. Chem. Int. Ed. 2017; 56: 2429
13g Trifonova EA, Ankudinov NM, Mikhaylov AA, Chusov DA, Nelyubina YV, Perekalin DS. Angew. Chem. Int. Ed. 2018; 57: 7714
13h Wang S.-G, Park SH, Cramer N. Angew. Chem. Int. Ed. 2018; 57: 5459
13i Liang H, Vasamsetty L, Li T, Jiang J, Pang X, Wang J. Chem. Eur. J. 2020; in press;

For selected examples, see:

14a Ye B, Cramer N. Angew. Chem. Int. Ed. 2014; 53: 7896
14b Dieckmann M, Jang Y.-S, Cramer N. Angew. Chem. Int. Ed. 2015; 54: 1214
14c Li T, Zhou C, Yan X, Wang J. Angew. Chem. Int. Ed. 2018; 57: 4048
14d Shan G, Flegel J, Li H, Merten C, Ziegler S, Antonchick AP, Waldmann H. Angew. Chem. Int. Ed. 2018; 57: 14250
14e Tian M, Bai D, Zheng G, Chang J, Li X. J. Am. Chem. Soc. 2019; 141: 9527
14f Duchemin C, Cramer N. Chem. Sci. 2019; 10: 2773
14g Li H, Gontla R, Flegel J, Merten C, Ziegler S, Antonchick AP, Waldmann H. Angew. Chem. Int. Ed. 2019; 58: 307
14h Ozols K, Jang Y.-J, Cramer N. J. Am. Chem. Soc. 2019; 141: 5675
14i Zheng G, Zhou Z, Zhu G, Zhai S, Xu H, Duan X, Yi W, Li X. Angew. Chem. Int. Ed. 2020; 59: 2890
14j Cui W.-J, Wu Z.-J, Gu Q, You S.-L. J. Am. Chem. Soc. 2020; 142: 7379
14k Mas-Rosello J, Smejkal T, Cramer N. Science 2020; 368: 1098
14l Shaaban S, Li H, Otte F, Strohmann C, Antonchick AP, Waldmann H. Org. Lett. 2020; in press;

15 Semakul M, Jackson KE, Paton RS, Rovis T. Chem. Sci. 2017; 8: 1015
16 It is important to mention that the use of a cyclopropene with two electron-withdrawing groups with RhJasCp failed in forming the ring-opening product in a reaction reported by the group of Rovis: Hyster TK, Rovis T. Synlett 2013; 24: 1842
17 Merten C, Golub TP, Kreienborg NM. J. Org. Chem. 2019; 84: 8797

18a Krämer K, Leong P, Lautens M. Org. Lett. 2011; 13: 819
18b Phan DH. T, Kou KG. M, Dong VM. J. Am. Chem. Soc. 2010; 132: 16354

19a Halgren TA. J. Comput. Chem. 1996; 17: 490
19b Spartan 14 . Wavefunction Inc; Irvine (CA, USA): 2014
19c Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Scalmani G, Barone V, Mennucci B, Petersson GA, Nakatsuji H, Caricato M, Li X, Hratchian HP, Izmaylov AF, Bloino J, Zheng G, Sonnenberg JL, Hada M, Ehara M, Toyota K, Fukuda R, Hasegawa J, Ishida M, Nakajima T, Honda Y, Kitao O, Nakai H, Vreven T, Montgomery JJ. A, Peralta JE, Ogliaro F, Bearpark M, Heyd JJ, Brothers E, Kudin KN, Staroverov VN, Keith T, Kobayashi R, Normand J, Raghavachari K, Rendell A, Burant JC, Iyengar SS, Tomasi J, Cossi M, Rega N, Millam JM, Klene M, Knox JE, Cross JB, Bakken V, Adamo C, Jaramillo J, Gomperts R, Stratmann RE, Yazyev O, Austin AJ, Cammi R, Pomelli C, Ochterski JW, Martin RL, Morokuma K, Zakrzewski VG, Voth GA, Salvador P, Dannenberg JJ, Dapprich S, Daniels AD, Farkas O, Foresman JB, Ortiz JV, Cioslowski J, Fox DJ. Gaussian 09, Revision E.01 . Gaussian, Inc; Wallingford (CT, USA): 2013

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