Harnessing the Versatile Reactivity of Propargyl Alcohols and their Derivatives for Sustainable Complex Molecule Synthesis

Benjamin James Ayers; Philip Wai Hong Chan

doi:10.1055/s-0034-1380402

Synlett, Table of Contents

Synlett 2015; 26(10): 1305-1339
DOI: 10.1055/s-0034-1380402

account

Harnessing the Versatile Reactivity of Propargyl Alcohols and their Derivatives for Sustainable Complex Molecule Synthesis

Benjamin James Ayers

^aDivision of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore 637371, Singapore

,

Philip Wai Hong Chan*

^aDivision of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore 637371, Singapore

^bSchool of Chemistry, Monash University, Clayton 3800, Victoria, Australia Email: phil.chan@monash.edu

^cDepartment of Chemistry, University of Warwick, Coventry, CV4 7AL, UK Email: P.W.H.Chan@warwick.ac.uk

› Author Affiliations

Abstract

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Abstract

One of the major challenges faced in modern synthetic chemistry is the efficient and selective assembly of complex molecular structures, especially carbo- and heterocycles, from readily accessible starting materials. With this has arisen the development of tandem reaction processes, which permit multiple transformations in a single synthetic step and that have often provided elegant routes to complex target scaffolds from simple precursors. Propargyl alcohols and their derivatives have become increasingly attractive starting materials for such processes owing to their reactivity in the presence of a Brønsted or Lewis acid catalyst as well as halogenation reagents. This account describes our recent efforts in the field, and demonstrates how propargyl alcohols and their derivatives can be transformed into a diverse range of highly functionalized acyclic, carbocyclic and heterocyclic structures, which are of importance as synthetic building blocks and as motifs in functional materials and bioactive compounds.

1 Introduction

2 Acyclic Conjugated Enynes

3 Carbocycles

3.1 Indenes

3.2 Dihydrofluorenes

3.3 Cyclopentenes, Cyclobutenes and Cyclopenta[b]naphthalenes

3.4 ortho-Phenolic Esters

4 Heterocycles with One Heteroatom

4.1 Indoles

4.2 Piperidines, Azepines and Pyrrolidines

4.3 Pyrroles

4.4 Furans

4.5 Benzo[b]oxepines and Benzo[b]azepines

5 Heterocycles with Two Heteroatoms

5.1 Thiazoles and Oxazoles

5.2 Dioxolanes

6 Conclusion

Key words

alkynes - carbocycles - heterocycles - homogeneous catalysis - tandem reactions

Full Text

References

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For selected examples concerning azabicyclo[4.2.0]octa-1(8),5-dienes, see:

47a Hu J, Tian B, Wu X, Tong X. Org. Lett. 2012; 14: 5074
47b Saito N, Tanaka Y, Sato Y. Org. Lett. 2009; 11: 4124
47c Mukai C, Hara Y, Miyashita Y, Inagaki F. J. Org. Chem. 2007; 72: 4454

48 Wang W, Hammond GB, Xu BJ. J. Am. Chem. Soc. 2012; 134: 5697
49 Rao W, , Sally Berry SN, Chan PW. H. Chem. Eur. J. 2014; 20: 13174
50 For the only known example of a cycloisomerization of 1,6,8-dienynes into cyclohexa-1,4-dienes under gold catalysis, see: Kim SM, Park JH, Chung YK. Chem. Commun. 2011; 47: 6719

51a Yeon H.-S, So E, Shin S. Chem. Eur. J. 2011; 17: 1764
51b Nakamura I, Yamagishi U, Song D, Konta S, Yamamoto Y. Chem. Asian J. 2008; 3: 285
51c Nakamura I, Yamagishi U, Song D, Konta S, Yamamoto Y. Angew. Chem. Int. Ed. 2007; 46: 2284

52 Teo WT, Rao W, Koh MJ, Chan PW. H. J. Org. Chem. 2013; 78: 7508

For recent examples illustrating pyrrole synthesis, see:

53a Chang M.-Y, Cheng Y.-C, Lu Y.-J. Org. Lett. 2014; 16: 6252
53b Gujarathi S, Liu X, Song L, Hendrickson H, Zheng G. Tetrahedron 2014; 70: 5267
53c Yang W, Zhou Y, Sun H, Zhang L, Zhao F, Liu H. RSC Adv. 2014; 68: 1113
53d Billedeau RJ, Klein KR, Kaplan D, Lou Y. Org. Lett. 2013; 15: 1421
53e Chen F, Shen T, Cui Y, Jiao N. Org. Lett. 2012; 14: 4926
53f Thompson BB, Montgomery J. Org. Lett. 2011; 13: 3289
53g Aginagalde M, Bello T, Masdeu C, Vara Y, Arrieta A, Cossio Fernando P. J. Org. Chem. 2010; 75: 7435
53h Ackermann L, Sandmann R, Kaspar LT. Org. Lett. 2009; 11: 2031
53i St Cyr DJ, Arndtsen BA. J. Am. Chem. Soc. 2007; 129: 12366
53j Binder JT, Kirsch SF. Org. Lett. 2006; 8: 2151

54 Zhang X, Teo JW, Ma D.-L, Leung C.-H, Chan PW. H. Tetrahedron Lett. 2014; 55: 6703
55 For representative examples, see refs 25c and 32a.
56 Aponick A, Li C.-Y, Palmes JA. Org. Lett. 2009; 11: 121

For selected reviews concerning furan motifs, see:

57a Lorente A, Lamariano-Merketegi J, Albericio F, Alvarez M. Chem. Rev. 2013; 113: 4567
57b Wong HN. C, Hou X.-L, Yeung K.-S, Huang H In Modern Heterocyclic Chemistry . Alvarez-Builla J, Vaquero JJ, Barluenga J. Wiley-VCH; Weinheim: 2011: 533
57c Boto A, Alvarez L In Heterocycles in Natural Product Synthesis . Majumdar KC, Chattopadhyay SK. Wiley-VCH; Weinheim: 2010: 99
57d Senning A In Comprehensive Heterocyclic Chemistry III . Katritzky AR, Rees CW, Scriven EF. V, Taylor RJ. K. Pergamon; New York: 2008: 389
57e The Chemistry of Heterocycles: Structures, Reactions, Synthesis, and Applications. Eicher T, Hauptmann S. Wiley-VCH; Weinheim: 2003
57f Wright DL. Chem. Innov. 2001; 31: 17

For selected examples illustrating furan synthesis, see:

58a Palisse A, Kirsch SF. Eur. J. Org. Chem. 2014; 7095
58b Yue Y, Zhang Y, Song W, Zhang X, Liu J, Zhou K. Adv. Synth. Catal. 2014; 356: 2459
58c Chen Z.-W, Luo M.-T, Wen Y.-L, Zhou Z.-G, Liu L.-X. Synlett 2014; 25: 2341
58d Hoffmann M, Miaskiewicz S, Weibel J.-M, Pale P, Blanc A. Beilstein J. Org. Chem. 2013; 9: 1774
58e Cao H, Zhan H, Cen J, Lin Y, Zhu Q, Fu M, Jiang H. Org. Lett. 2013; 15: 1080
58f Li E, Cheng X, Wang C, Shao Y, Li Y. J. Org. Chem. 2012; 77: 7744
58g Umland K.-D, Palisse A, Haug TT, Kirsch SF. Angew. Chem. Int. Ed. 2011; 50: 9965
58h Li W, Zhang J. Chem. Commun. 2010; 46: 8839
58i Cao H, Jiang H, Yao W, Liu X. Org. Lett. 2009; 11: 1931
58j Feng X, Tan Z, Chen D, Shen Y, Guo C.-C, Xiang J, Zhu C. Tetrahedron Lett. 2008; 49: 4110
58k Jung HH, Floreancig PE. J. Org. Chem. 2007; 72: 7359
58l Suhre MH, Reif M, Kirsch SF. Org. Lett. 2005; 7: 3925

59 Mothe SR, Lauw SJ. L, Kothandaraman P, Chan PW. H. J. Org. Chem. 2012; 77: 6937

For selected examples, see:

60a Kashima K, Sano K, Yun YS, Ina H, Kunugi A, Inoue H. Chem. Pharm. Bull. 2010; 58: 191
60b Kim S, Su B.-N, Riswan S, Kardono LB. S, Afriastini JJ, Gallucci JC, Chai H, Farnsworth NR, Cordell GA, Swanson SM, Kinghorn AD. Tetrahedron Lett. 2005; 46: 9021
60c Engler M, Anke T, Sterner OJ. J. Antibiot. 1997; 50: 330
60d Engler M, Anke T, Sterner OJ, Brandt UJ. J. Antibiot. 1997; 50: 325
60e Macías FA, Molinillo JM. G, Varela RM, Torres A, Fronczek FR. J. Org. Chem. 1994; 59: 8261
60f Asakawa Y, Hashimoto T, Takikawa K, Tori M, Ogawa S. Phytochemistry 1991; 30: 235

For recent selected examples, see:

61a Bera K, Jalal S, Sarkar S, Jana U. Org. Biomol. Chem. 2014; 12: 57
61b Rohlmann R, Daniliuc C.-G, Mancheno OG. Chem. Commun. 2013; 49: 11665
61c Choi YL, Lim HS, Lim HJ, Heo J.-N. Org. Lett. 2012; 14: 5102
61d Liu J, Liu Y. Org. Lett. 2012; 14: 4742
61e Varela-Fernandéz A, Garcia-Yebra C, Varela JA, Esteruelas MA, Saa C. Angew. Chem. Int. Ed. 2010; 49: 4278
61f Majumdar KC, Sinha B, Ansary I, Chakraborty S. Synlett 2010; 1407

62 Sze EM. L, Rao W, Koh MJ, Chan PW. H. Chem. Eur. J. 2011; 17: 1437

For selected examples, see:

63a Yea CM, Allan CE, Ashworth DM, Barnett J, Baxter AJ, Broadbridge JD, Franklin RJ, Hampton SL, Hudson P, Horton JA, Jenkins PD, Penson AM, Pitt GR. W, Rivière P, Robson PA, Rooker DP, Semple G, Sheppard A, Haigh RM, Roe MB. J. Med. Chem. 2008; 51: 8124
63b Xiang MA, Rybczynski PJ, Patel M, Chen RH, McComsey DF, Zhang H.-C, Gunnet JW, Look R, Wang Y, Minor LK, Zhong HM, Villani FJ, Demarest KT, Damianob BP, Maryanoff BE. Bioorg. Med. Chem. Lett. 2007; 17: 6623
63c Nakamura S, Yamamura Y, Itoh S, Hirano T, Tsujimae K, Aoyama M, Kondo K, Ogawa H, Shinohara T, Kan K, Tanada Y, Teramoto S, Sumida T, Nakayama S, Sekiguchi K, Kambe T, Tsujimoto G, Mori T, Tominaga M. Br. J. Pharmacol. 2000; 129: 1700
63d Yamamura Y, Nakamura S, Ito S, Hirano T, Onogawa T, Yamashita T, Yamada Y, Tsujimae K, Aoyama M, Kotosai K, Ogawa H, Yamashita H, Kondo K, Tominaga M, Tsujimoto G, Mori T. J. Pharmacol. Exp. Ther. 1998; 287: 860

For recent selected examples, see:

64a Jalal S, Bera K, Sarkar S, Paul K, Jana U. Org. Biomol. Chem. 2014; 12: 1759
64b Benedetti E, Lornazzi M, Tibiletti F, Goddard J.-P, Fensterbank L, Malacria M, Palmisano G, Penoni A. Synthesis 2012; 44: 3523
64c Wang L, Huang J, Peng S, Liu H, Jiang X, Wang J. Angew. Chem. Int. Ed. 2013; 53: 1768
64d Kothandaraman P, Huang C, Susanti D, Rao W, Chan PW. H. Chem. Eur. J. 2011; 17: 10081
64e He H, Liu W.-B, Dai L.-X, You S.-L. Angew. Chem. Int. Ed. 2010; 49: 1496
64f González-Gómez Á, Domínguez G, Pérez-Castells J. Eur. J. Org. Chem. 2009; 5057

65 Sze EL. M, Koh MJ, Tjia YM, Rao W, Chan PW. H. Tetrahedron 2013; 69: 5558

For selected reviews, see:

66a Just-Baringo X, Albericio F, Alvarez M. Curr. Top. Med. Chem. 2014; 14: 1244
66b Jin Z. Nat. Prod. Rep. 2013; 30: 869
66c Heterocyclic Chemistry in Drug Discovery . Li JJ. John Wiley & Sons; Hoboken: 2013
66d Walsh CT, Malcolmson SJ, Young TS. ACS Chem. Biol. 2012; 7: 429
66e Tomer I, Mishra R, , Priyanka Sharma NK, Jha KK. J. Pharm. Res. 2011; 4: 2975
66f Turner CD, Liang HS. Curr. Org. Chem. 2011; 15: 2846
66g Revuelta J, Machetti F, Cicchi S In Modern Heterocyclic Chemistry . Alvarez-Builla J, Vaquero JJ, Barluenga J. Wiley-VCH; Weinheim: 2011: 809
66h Davyt D, Serra G. Mar. Drugs 2010; 8: 2755

67a Gao X, Pan Y.-M, Lin M, Chen L, Zhan Z.-P. Org. Biomol. Chem. 2010; 8: 3259
67b Yoshimatsu M, Yamamoto T, Sawa A, Kato T, Tanabe G, Muraoka O. Org. Lett. 2009; 11: 2952

68 Zhang X, Teo WT, , Sally Chan PW. H. J. Org. Chem. 2010; 75: 6290

69a Kumar MP, Liu R.-S. J. Org. Chem. 2006; 71: 4951
69b Milton MD, Inada Y, Nishibayashi Y, Uemura S. Chem. Commun. 2004; 2712

70 Zhang X, Teo WT, Chan PW. H. J. Organomet. Chem. 2011; 696: 331
71 Pan Y.-M, Zheng F.-J, Lin H.-X, Zhan Z.-P. J. Org. Chem. 2009; 74: 3148

72a Huple DB, Liu R.-S. Chem. Commun. 2012; 48: 10975
72b Molawi K, Delpont N, Echavarren AM. Angew. Chem. Int. Ed. 2010; 49: 3517
72c Schelweis M, Moser R, Dempwolff AL, Rominger F, Helmchen G. Chem. Eur. J. 2009; 15: 10888
72d Escribano-Cuesta A, López-Carrillo V, Janssen D, Echavarren AM. Chem. Eur. J. 2009; 15: 5646
72e Shelweis M, Dempwolff AL, Rominger F, Helmchen G. Angew. Chem. Int. Ed. 2007; 46: 5598
72f Jiménez-Núnez E, Claverie CK, Nieto-Oberhuber C, Echavarren AM. Angew. Chem. Int. Ed. 2006; 45: 5452