Metal-Catalyzed Cyclizations to Pyran and Oxazine Derivatives

Jesús A. Varela; Carlos Saá

doi:10.1055/s-0035-1562466

Synthesis, Table of Contents

Synthesis 2016; 48(20): 3470-3478
DOI: 10.1055/s-0035-1562466

short review

Metal-Catalyzed Cyclizations to Pyran and Oxazine Derivatives

Jesús A. Varela

Centro Singular de Investigación en Química Biolóxica e Materiais Moleculares (CIQUS) e Departamento de Química Orgánica, Universidade de Santiago de Compostela, 15782 Santiago de Compostela, Spain Email: carlos.saa@usc.es

,

Carlos Saá*

Centro Singular de Investigación en Química Biolóxica e Materiais Moleculares (CIQUS) e Departamento de Química Orgánica, Universidade de Santiago de Compostela, 15782 Santiago de Compostela, Spain Email: carlos.saa@usc.es

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Abstract

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Abstract

Pyrans are privileged heterocyclic structures found in numerous natural compounds with extraordinary biological activities. The synthesis of these relevant structures has attracted a great deal of attention over the years. Catalytic methodologies based on the activation of neutral unsaturated functionalities of acyclic compounds that undergo intramolecular cyclizations have achieved prominent synthetic relevance. In this short review, we discuss the successful construction of dihydropyran and dihydro-1,4-oxazine derivatives from acyclic precursors by metal-catalyzed intramolecular cyclizations through carbon–carbon, carbon–oxygen, and carbon–nitrogen bond formation. Remarkable synthetic applications are highlighted.

1 Introduction

2 3,4-Dihydropyrans

3 3,4-Dihydro-1,4-oxazines

4 3,6-Dihydropyrans

5 Synthetic Applications

6 Summary

Key words

allenols - bis-homopropargyl alcohols - catalysis - cyclizations - heterocyclizations - 1,4-oxazines - pyrans - transition metals

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References

References

1a Fravel BW. Pyrans and Their Benzo Derivatives: Applications . In Comprehensive Heterocyclic Chemistry III . Vol. 7. Katritzky AR, Ramsden CA, Scriven EF. V, Taylor RJ. K. Elsevier; Dordrecht: 2008: 701
1b Elliott MC. J. Chem. Soc., Perkin Trans. 1 2002; 2301
1c Elliott MC, Williams E. J. Chem. Soc., Perkin Trans. 1 2001; 2303
1d Elliott MC. J. Chem. Soc., Perkin Trans. 1 2000; 1291
1e Mitchinson A, Nadin A. J. Chem. Soc., Perkin Trans. 1 2000; 2862
1f Boivin TL. B. Tetrahedron 1987; 43: 3309

2a Kurahashi T, Matsubara S. Acc. Chem. Res. 2015; 48: 1703
2b Cornil J, Gonnard L, Bensoussan C, Serra-Muns A, Gnamm C, Commandeur C, Commandeur M, Reymond S, Guerinot A, Cossy J. Acc. Chem. Res. 2015; 48: 761
2c Synthesis of Heterocycles via Metal-Catalyzed Reactions that Generate One or More Carbon-Heteroatom Bonds. Wolfe JP. Springer; Heidelberg: 2013
2d Alcaide B, Almendros P, Alonso JM. Org. Biomol. Chem. 2011; 9: 4405
2e Hintermann L. Top. Organomet. Chem. 2010; 31: 123
2f Larrosa I, Romea P, Urpí F. Tetrahedron 2008; 64: 2683
2g Alonso F, Beletskaya IP, Yus M. Chem. Rev. 2004; 104: 3079
2h Beller M, Seayad J, Tillack A, Jiao H. Angew. Chem. Int. Ed. 2004; 43: 3368

3 For a special issue edited by P. A. Clarke, see: Tetrahedron 2011; 67: 4949

4a Smoot JT, Demchenko AV. Adv. Carbohydr. Chem. Biochem. 2009; 62: 161
4b Boltje TJ, Buskas T, Boons G.-J. Nat. Chem. 2009; 1: 611
4c Schmidt RR, Vankar YD. Acc. Chem. Res. 2008; 41: 1059
4d Ramesh NG, Balasubramanian KK. Eur. J. Org. Chem. 2003; 4477
4e Seeberger PH, Bilodeau MT, Danishefsky SJ. Aldrichimica Acta 1997; 30: 75

5a Yu B, Wang L.-X, Danishefsky S, Crich D. Carbohydrate Synthesis towards Glycobiology . Ding K, Dai L.-X. Wiley-VCH; Weinheim: 2012
5b Nicolaou KC, Mitchell HJ. Angew. Chem. Int. Ed. 2001; 40: 1576
5c Sears P, Wong C.-H. Science (Washington, D.C.) 2001; 291: 2344

6a Taylor RD, MacCoss M, Lawson AD. G. J. Med. Chem. 2014; 57: 5845
6b Fox BM, Sugimoto K, Iio K, Yoshida A, Zhang J, Li K, Hao X, Labelle M, Smith M.-L, Rubenstein SM, Ye G, McMinn D, Jackson S, Choi R, Shan B, Ma J, Miao S, Matsui T, Ogawa N, Suzuki M, Kobayashi A, Ozeki H, Okuma C, Ishii Y, Tomimoto D, Furakawa N, Tanaka M, Matsushita M, Takahashi M, Inaba T, Sagawa S, Kayser F. J. Med. Chem. 2014; 57: 3464
6c Matralis AN, Kourounakis AP. J. Med. Chem. 2014; 57: 2568
6d Li W, Duan X, Yan H, Xin H. Org. Biomol. Chem. 2013; 11: 4546
6e Kourounakis AP, Charitos C, Rekka EA, Kourounakis PN. J. Med. Chem. 2008; 51: 5861

7 Varela-Fernández A, González-Rodríguez C, Varela JA, Castedo L, Saá C. Org. Lett. 2009; 11: 5350

8a Thansandote P, Chong E, Feldmann K.-O, Lautens M. J. Org. Chem. 2010; 75: 3495
8b Kundu NG, Chaudhuri G, Upadhyay A. J. Org. Chem. 2001; 66: 20

9a Varela JA, González-Rodríguez C, Saá C. Top. Organomet. Chem. 2014; 48: 237
9b Trost BM, McClory A. Chem. Asian J. 2008; 3: 164
9c Metal Vinylidenes and Allenylidenes in Catalysis: From Reactivity to Applications in Synthesis. Bruneau C, Dixneuf P. Wiley-VCH; Weinheim: 2008
9d Bruneau C, Dixneuf PH. Angew. Chem. Int. Ed. 2006; 45: 2176

10a McDonald FE, Reddy KS. J. Organomet. Chem. 2001; 617–618: 444
10b McDonald FE, Reddy KS, Díaz Y. J. Am. Chem. Soc. 2000; 122: 4304
10c McDonald FE. Chem. Eur. J. 1999; 5: 3103

11 Trost BM, Rhee YH. J. Am. Chem. Soc. 2002; 124: 2528
12 Liu PN, Su FH, Wen TB, Sung HH. Y, Williams ID, Jia G. Chem. Eur. J. 2010; 16: 7889
13 Zacuto MJ, Tomita D, Pirzada Z, Xu F. Org. Lett. 2010; 12: 684
14 Trost BM, Rhee YH. J. Am. Chem. Soc. 2003; 125: 7482
15 Fujino D, Yorimitsu H, Osuka A. J. Am. Chem. Soc. 2014; 136: 6255
16 Trost BM, Frontier AJ. J. Am. Chem. Soc. 2000; 122: 11727
17 Silva F, Reiter M, Mills-Webb R, Sawicki M, Klar D, Bensel N, Wagner A, Gouverneur V. J. Org. Chem. 2006; 71: 8390

18a Baker-Glenn C, Hodnett N, Reiter M, Ropp S, Ancliff R, Gouverneur V. J. Am. Chem. Soc. 2005; 127: 1481
18b Reiter M, Turner H, Mills-Webb R, Gouverneur V. J. Org. Chem. 2005; 70: 8478
18c Reiter M, Ropp S, Gouverneur V. Org. Lett. 2004; 6: 91

19 Cambeiro F, López S, Varela JA, Saá C. Angew. Chem. Int. Ed. 2014; 53: 5959
20 Lee AL, Malcolmson SJ, Puglisi A, Schrock RR, Hoveyda AH. J. Am. Chem. Soc. 2006; 128: 5153
21 Lv L, Xi H, Bai X, Li Z. Org. Lett. 2015; 17: 4324

22a Bogacki R, Gill DM, Kerr WJ, Lamont S, Parkinson JA, Paterson LC. Chem. Commun. 2013; 49: 8931
22b Brice H, Gill DM, Goldie L, Keegan PS, Kerr WJ, Svensson PH. Chem. Commun. 2012; 48: 4836

23 Kalepu J, Katukojvala S. Angew. Chem. Int. Ed. 2016; 55 in press; DOI: 10.1002/anie.201600878
24 Ma X, Pan S, Wang H, Chen W. Org. Lett. 2014; 16: 4554
25 Zulys A, Dochnahl M, Hollmann D, Loehnwitz K, Herrmann J.-S, Roesky PW, Blechert S. Angew. Chem. Int. Ed. 2005; 44: 7794
26 Arai MA, Kuraishi M, Arai T, Sasai H. J. Am. Chem. Soc. 2001; 123: 2907
27 Gockel B, Krause N. Org. Lett. 2006; 8: 4485
28 Zriba R, Gandon V, Aubert C, Fensterband L, Malacria M. Chem. Eur. J. 2008; 14: 1482

29a Alcaide B, Almendros P, Carrascosa R, Martínez del Campo T. Chem. Eur. J. 2010; 16: 13243
29b Alcaide B, Almendros P, Martínez del Campo T, Soriano E, Marco-Contelles JL. Chem. Eur. J. 2009; 15: 9127

30 Pawliczek M, Schneider TF, Maass C, Stalke D, Werz DB. Angew. Chem. Int. Ed. 2015; 54: 4119
31 Trost BM, Ashfeld BL. Org. Lett. 2008; 10: 1893
32 Trost BM, Frontier AJ, Thiel OR, Yang H, Dong G. Chem. Eur. J. 2011; 17: 9762
33 Liao X, Zhou H, Wearing XZ, Ma J, Cook JM. Org. Lett. 2005; 7: 3501
34 Sawama Y, Sawama Y, Krause N. Org. Biomol. Chem. 2008; 6: 3573