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Synthesis 2022; 54(19): 4167-4183
DOI: 10.1055/a-1843-1954
DOI: 10.1055/a-1843-1954
short review
Recent Developments in Transannular Reactions
This work was supported by the Spanish Agencia Estatal de Investigación (FEDER-PID2020-118422-GB-I00) and the Basque Government (Grupos IT908-16).
Dedicated to Prof. Dr. Joan Bosch on the occasion of his 75th birthday
Abstract
Transannular reactions have shown a remarkable performance for the construction of polycyclic scaffolds from medium- or large-sized cyclic molecules in an unconventional manner. Recent examples of transannular reactions reported from 2011 have been reviewed, emphasizing the excellent performance of this approach when accessing the target compounds. This review also highlights how this methodology provides an alternative approach to other commonly used strategies for the construction of cyclic entities such as cyclization or cycloaddition reactions.
1 Introduction
2 Transannular Cycloadditions and Electrocyclizations
3 Transannular Conjugate Additions
4 Transannular 1,2-Addition to Ketones, Imines, Esters, and Amides
5 Transannular Reactions via Electrophilic Activation of Olefins
6 Transannular Ring-Opening of Epoxides
7 Transannular Alkylations of Enolates and Related Species
8 Miscellaneous Transannular Reactions
9 Concluding Remarks
Key words
transannular reaction - bicyclic compounds - cyclization - fused-ring systems - heterocycles - macrocycles - natural products - total synthesisPublication History
Received: 28 March 2022
Accepted after revision: 04 May 2022
Accepted Manuscript online:
04 May 2022
Article published online:
21 July 2022
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References
- 1a Haufe G, Muehlstaedt M. Z. Chem. 1979; 19: 170
- 1b Handa S, Pattenden G. Contemp. Org. Synth. 1997; 4: 196
- 1c Marsault E, Toro A, Nowak P, Deslongchamps P. Tetrahedron 2001; 57: 4243
- 1d Montana AM, Batalla C, Barcia JA. Curr. Org. Chem. 2009; 13: 919
- 1e Rizzo A, Harutyunyan SR. Org. Biomol. Chem. 2014; 12: 6570
- 2a Appavoo SD, Huh S, Diaz DB, Yudin AK. Chem. Rev. 2019; 119: 9724
- 2b Gleiter R, Haberhauer G. Eur. J. Org. Chem. 2018; 2406
- 2c Rademacher P. Chem. Soc. Rev. 1995; 24: 143
- 3a Reyes E, Uria U, Carrillo L, Vicario JL. Tetrahedron 2014; 70: 9461
- 3b Clarke PA, Reeder AT, Winn J. Synthesis 2009; 691
- 3c Adio AM. Tetrahedron 2009; 65: 1533
- 3d See also: ref 1c
- 4 Deslongchamps P. Pure Appl. Chem. 1992; 64: 1831
- 5 Iafe RG, Kuo JL, Hochstatter DG, Saga T, Turner JW, Merlic CA. Org. Lett. 2013; 15: 582
- 6a He CQ, Chen TQ, Patel A, Karabiyikoglu S, Merlic CA, Houk KN. J. Org. Chem. 2015; 80: 11039
- 6b Karabiyikoglu S, Merlic CA. Org. Lett. 2015; 17: 4086
- 6c Prathyusha V, Priyakumar UD. RSC Adv. 2013; 3: 15892
- 7 Nicolaou KC, Shah AA, Korman H, Khan T, Shi L, Worawalai W, Theodorakis EA. Angew. Chem. Int. Ed. 2015; 54: 9203
- 8 Maiga-Wandiam B, Corbu A, Massiot G, Sautel F, Yu P, Lin BW.-Y, Houk KN, Cossy J. J. Org. Chem. 2018; 83: 5975
- 9 Breunig M, Yuan P, Gaich T. Angew. Chem. Int. Ed. 2020; 59: 5521
- 10a Li Y, Palframan MJ, Pattenden G, Winne JM. Tetrahedron 2014; 70: 7229
- 10b See also: Vasamsetty L, Khan FA, Mehta G. Tetrahedron Lett. 2014; 55: 7068
- 11 Kim HJ, Ruszczycky MW, Choi S, Liu Y, Liu H. Nature 2011; 473: 109
- 12 Mergott DJ, Frank SA, Roush WR. Proc. Natl. Acad. Sci. U. S. A. 2004; 101: 11955
- 13 Patel A, Chen Z, Yang Z, Gutiérrez O, Liu H, Houk KN, Singleton DA. J. Am. Chem. Soc. 2016; 138: 3631
- 14a Yu P, Patel A, Houk KN. J. Am. Chem. Soc. 2015; 137: 13518
- 14b Zhang C, Wang X, Chen Y, He Z, Yu P, Liang Y. J. Org. Chem. 2020; 85: 9440
- 15 Campbell EL, Skepper CK, Sankar K, Duncan KK, Boger DL. Org. Lett. 2013; 15: 5306
- 16a Chan D, Chen Y, Low K.-H, Chiu P. Chem. Eur. J. 2018; 24: 2375
- 16b Ma R, Gung BW. Tetrahedron 2020; 76: 130840
- 17 Zhurakovskyi O, Ellis SR, Thompson AL, Robertson J. Org. Lett. 2017; 19: 2174
- 18 Sendra J, Reyes E, Prieto L, Fernández E, Vicario JL. Org. Lett. 2021; 23: 8738
- 19a Balskus EP, Jacobsen EN. Science 2007; 317: 1736
- 19b See also: Jaschinski T, Hiersemann M. Org. Lett. 2012; 14: 4114
- 19c Chandler CL, List B. J. Am. Chem. Soc. 2008; 130: 6737
- 20 Takao K, Kai H, Yamada A, Fukushima Y, Komatsu D, Ogura A, Yoshida K. Angew. Chem. Int. Ed. 2019; 58: 9851
- 21a Fukazawa A, Ohshima H, Shiota Y, Takahashi S, Yoshizawa K, Yamaguchi S. J. Am. Chem. Soc. 2013; 135: 1731
- 21b Fukazawa A, Ohshima H, Shimizu S, Kobayashi N, Yoshizawa K, Yamaguchi S. J. Am. Chem. Soc. 2014; 136: 8738
- 22a Ohshima H, Fukazawa A, Sasamori T, Yamaguchi S. Angew. Chem. Int. Ed. 2015; 54: 7636
- 22b Nakai A, Kim J, Tanaka T, Kim D, Osuka A. Angew. Chem. Int. Ed. 2021; 60: 26540
- 22c Eisch JJ, Yu K, Rheingold AL. Eur. J. Org. Chem. 2014; 818
- 23 Nobusue S, Yamane H, Miyoshi H, Tobe Y. Org. Lett. 2014; 16: 1940
- 24a Li Y, Pattenden G. Tetrahedron 2011; 67: 10045
- 24b Meng Z, Fürstner A. J. Am. Chem. Soc. 2019; 141: 805
- 25 Han J, Li F, Li C. J. Am. Chem. Soc. 2014; 136: 13610
- 26a Roosen PC, Vanderwal CD. Org. Lett. 2014; 16: 4368
- 26b Ramella V, Roosen PC, Vanderwal CD. Org. Lett. 2020; 22: 2883
- 27 Thornton PD, Cameron TS, Burnell DJ. Org. Biomol. Chem. 2011; 9: 3447
- 28 Martínez-García L, Prado G, Gómez KV, Paleo MR, Sardina FJ. J. Org. Chem. 2021; 86: 13684
- 29 Fujii T, Nakada M. Tetrahedron Lett. 2014; 55: 1597
- 30a Xue H, Yang J, Gopal P. Org. Lett. 2011; 13: 5696
- 30b Xue H, Gopal P, Yang J. J. Org. Chem. 2012; 77: 8933
- 31 Nguyen QN. N, Yang J, Tantillo DJ. J. Org. Chem. 2014; 79: 7162
- 32 Umihara H, Yoshino T, Shimokawa J, Kitamura M, Fukuyama T. Angew. Chem. Int. Ed. 2016; 55: 6915
- 33a Zhu C, Liu Z, Chen G, Zhang K, Ding H. Angew. Chem. Int. Ed. 2015; 54: 879
- 33b Yu K, Gao B, Liu Z, Ding H. Chem. Commun. 2016; 52: 4485
- 34 Raps FC, Fäseke VC, Häussinger D, Sparr C. Angew. Chem. Int. Ed. 2020; 59: 18390
- 35 Mato R, Reyes E, Carrillo L, Uria U, Prieto L, Manzano R, Vicario JL. Chem. Commun. 2020; 56: 13149
- 36 Sendra J, Manzano R, Reyes E, Vicario JL, Fernández E. Angew. Chem. Int. Ed. 2020; 59: 2100
- 37 Mato R, Manzano R, Reyes E, Carrillo L, Uria U, Vicario JL. J. Am. Chem. Soc. 2019; 141: 9495
- 38 Lee AS, Liau BB, Shair MD. J. Am. Chem. Soc. 2014; 136: 13442
- 39a Samame RA, Owens CM, Rychnovsky SD. Chem. Sci. 2016; 7: 188
- 39b Burtea A, DeForest J, Li X, Rychnovsky SD. Angew. Chem. Int. Ed. 2019; 58: 16193
- 39c Zhang J, Ya Y, Hu R, Li T, Bai W.-J, Yang Y. Angew. Chem. Int. Ed. 2020; 59: 2860
- 39d Ju X, Beaudry CM. Angew. Chem. Int. Ed. 2019; 58: 6752
- 40a Leitner C, Gaich T. Chem. Commun. 2017; 53: 7451
- 40b Yoshida K, Okada K, Ueda H, Tokuyama H. Angew. Chem. Int. Ed. 2020; 59: 23089
- 40c Delayre B, Piemontesi C, Wang Q, Zhu J. Angew. Chem. Int. Ed. 2020; 59: 13990
- 41 Antropow AH, García NR, White KL, Movassaghi M. Org. Lett. 2018; 20: 3647
- 42 Zeng X, Boger DL. J. Am. Chem. Soc. 2021; 143: 12412
- 43a Mewald M, Medley JW, Movassaghi M. Angew. Chem. Int. Ed. 2014; 53: 11634
- 43b White KL, Movassaghi M. J. Am. Chem. Soc. 2016; 138: 11383
- 43c Kang T, White KL, Mann TJ, Hoveyda AH, Movassaghi M. Angew. Chem. Int. Ed. 2017; 56: 13857
- 44 McMurray L, Beck EM, Gaunt MJ. Angew. Chem. Int. Ed. 2012; 51: 9288
- 45 Ohtawa M, Krambis MJ, Cerne R, Schkeryantz JM, Witkin JM, Shenvi RA. J. Am. Chem. Soc. 2017; 139: 9637
- 46 Minassi A, Pollastro F, Chianese G, Caprioglio D, Taglialatela-Scafati O, Appendino G. Angew. Chem. Int. Ed. 2017; 56: 7935
- 47 Tian C, Lei X, Wang Y, Dong Z, Liu G, Tang Y. Angew. Chem. Int. Ed. 2016; 55: 6992
- 48a Rajapaksa NS, Jacobsen EN. Org. Lett. 2013; 15: 4238
- 48b Riehl PS, Nasrallah DJ, Schindler CS. Chem. Sci. 2019; 10: 10267
- 49 Koshimizu M, Nagatomo M, Inoue M. Tetrahedron 2018; 74: 3384
- 50a Clarke PA, Winn J. Tetrahedron Lett. 2011; 52: 1469
- 50b Zhang J, Wang X, Xu T. Nat. Commun. 2021; 12: 3022
- 51a Cao F, Gao W, Wang X, Zhang Z, Yin G, Wang Y, Li Z, Shi T, Hou Y, Chen J, Wang Z. Org. Lett. 2021; 23: 6222
- 51b Shi T, Cao F, Chen J, Wang X, Yin G, Wang H, Wang Z. Org. Chem. Front. 2022; 9: 771
- 52 Williams DR, Mondal PK, Bawel SA, Nag PP. Org. Lett. 2014; 16: 1956
- 53a Dagoneau D, Xu Z, Wang Q, Zhu J. Angew. Chem. Int. Ed. 2016; 55: 760
- 53b Pfaffenbach M, Gaich T. Chem. Eur. J. 2015; 21: 6355
- 53c Yang Y, Bai Y, Sun S, Dai M. Org. Lett. 2014; 16: 6216
- 53d Yan Q, Carroll PJ, Gau MR, Winkler JD, Joullié MM. Org. Lett. 2019; 21: 6619
- 53e Li H, Wang X, Lei X. Angew. Chem. Int. Ed. 2012; 51: 491
- 54a Piemontesi C, Wang Q, Zhu J. J. Am. Chem. Soc. 2016; 138: 11148
- 54b See also: Huang J.-Z, Jie X.-K, Wei K, Zhang H, Wang M.-C, Yang Y.-R. Synlett 2013; 24: 1303
- 55a Cakmak M, Mayer P, Trauner D. Nat. Chem. 2011; 3: 543
- 55b Brock EA, Davies SG, Lee JA, Roberts PM, Thompson JE. Org. Lett. 2011; 13: 1594
- 56 Atmuri ND. P, Lubel WD. J. Org. Chem. 2020; 85: 1340
- 57 Bohland F, Erlin I, Platte L, Schröder M, Schollmeyer D, Nubbemeyer U. Eur. J. Org. Chem. 2014; 6272
- 58 Royzen M, Taylor MT, DeAngelis A, Fox JM. Chem. Sci. 2011; 2: 2162
- 59 Iqbal M, Black RJ. G, Winn J, Reeder AT, Blake AJ, Clarke PA. Org. Biomol. Chem. 2011; 9: 5062
- 60a Lekky A, Ruengsatra T, Ruchiwarat S, Ploypradith P. J. Org. Chem. 2019; 84: 5277
- 60b Tomooka K, Suzuki M, Shimada M, Ni R, Uehara K. Org. Lett. 2011; 13: 4926
- 61 Ohshima H, Fukazawa A, Yamaguchi S. Angew. Chem. Int. Ed. 2017; 56: 3270
- 62a Hibi D, Kitabayashi K, Shimizu A, Umeda R, Tobe Y. Org. Biomol. Chem. 2013; 11: 8256
- 62b See also: Takeda T, Inukai K, Tahara K, Tobe Y. J. Org. Chem. 2011; 76: 9116
- 63 Kreuzahler M, Fabig S, Haberhauer G, Gleiter R. J. Org. Chem. 2017; 82: 13572
- 64 Ushakov DB, Navickas V, Ströbele M, Maichle-Mössmer C, Sasse F, Maier ME. Org. Lett. 2011; 13: 2090
- 65 Biji M, Radhakrishnan KV, Lankalapalli RS. Org. Lett. 2021; 23: 5871
- 66 Rong Z.-Q, Yang L.-C, Liu S, Yu Z, Wang Y.-N, Tan ZY, Huang R.-Z, Lan Y, Zhao Y. J. Am. Chem. Soc. 2017; 139: 15304
- 67 Liu J, Zhou Y, Yu Z.-X. Org. Lett. 2022; 24: 1444
- 68a Liu X, Liu J, Wu J, Huang G, Liang R, Chung LW, Li C.-C. J. Am. Chem. Soc. 2019; 141: 2872
- 68b Liu X, Liu J, Li C.-C. J. Org. Chem. 2021; 86: 11125
- 69 Riaño I, Uria U, Reyes E, Carrillo L, Vicario JL. J. Org. Chem. 2018; 83: 4180
- 70a Lajiness JP, Boger DL. J. Org. Chem. 2011; 76: 583
- 70b Uematsu M, Boger DL. J. Org. Chem. 2014; 79: 9699
- 70c See also: Imaizumi T, Yamashita Y, Nakazawa Y, Okano K, Sakata J, Tokuyama H. Org. Lett. 2019; 21: 6185
- 71 Craig D, Funai K, Gore SJ, Kang A, Mayweg AV. W. Org. Biomol. Chem. 2011; 9: 8000
- 72 Lee KR, Ahn S, Lee S. Org. Lett. 2021; 23: 3735
- 73 Barnes TH, Johnson KF, Gorden JD, Merner BL. Chem. Commun. 2020; 56: 8747
- 74 Karabiyikoglu S, Boon BA, Merlic CA. J. Org. Chem. 2017; 82: 7732
For a computational study on an Au(I)-catalyzed reaction from allene/furane substrates reported, see:
Pioneering report:
For other examples of reductive transannular coupling reactions, see:
Similar transannular Michael reactions with macrocyclic unsaturated γ-lactones as internal acceptors have been proposed to happen in the biosynthesis of cembranoid diterpenes:
See also:
For a related achiral version, see:
For another example in which a transannular Prins-like reaction is invoked as part of a complex cascade reaction, see:
For other recent examples of transannular aminal formation in total synthesis, see:
For another example, see:
For other example involving a different approach for the generation of the carbocation is intermediate, see: