Oxygen-Tethered 1,6-Enynes and [4.1.0]-Bicyclic Ether Skeletons as Hedonic Materials for the Fragrance Industry

Abstract

The synthesis of original structures for the fragrance industry bearing bicyclic scaffolds is described. To the best of our knowledge, these structures are not found in the fragrance industry, neither from natural nor synthetic pathways. NHC–gold-type catalysts showed excellent activities leading to light bicyclic enol ethers. Several bicyclic adducts were prepared in good to excellent yields (18–99%). Evaluation of NHC–Au complexes allowed to reach a TOF of 300 h^–1. The evaluation for the organoleptic properties of [4.1.0]-bicyclic ethers were compared with the unprecedented properties of the 1,6-enyne precursors. Evaluations of starting materials showed a great interest in these structures with various olfactory facets. In this study, we depicted the similarity and differences between starting ethers and their cycloisomerized bicyclic counterparts.

Key words

gold catalysis - N-heterocyclic carbenes - fragrance - 1,6-enynes - bicyclic compounds

• References

• 1a de Feydeau E. Les Parfums: Histoire, Anthologie, Dictionnaire. Robert Laffont; Paris: 2011
• 1b Edwards M. Perfume Legends: French Feminine Fragrances . M. Edwards & Co. in association with HM Editions; Levallois: 1996
• 1c Armanino N, Charpentier J, Flachsmann F, Goeke A, Liniger A, Kraft P. Angew. Chem. Int. Ed. 2020; 59: 16310
• 2 Saudan L. Chimia 2019; 73: 684
• 3a Corbier BP, Teisseire PJ. US3953516A, 1976
• 3b Mookherjee BD, Narula AP. S, Patel SM, Arruda EM, Merritt PM. US7175871B2, 2007
• 4 Baudin J. US5332725A, 1994
• 5 Schröder F. Chem. Biodiversity 2014; 11: 1734
• 6 Goeke A. US20050042255A1, 2005
• 7 Schroder F. US8450533B2, 2013
• 8a The Chemistry of Fragrances: From Perfumer to Consumer. Sell CS. RSC Publishing; Cambridge: 2006
• 8b Sell CS. Chemistry and the Sense of Smell . Wiley; Hoboken: 2014
• 8c Ohloff G, Pickenhagen W, Kraft P. Scent and Chemistry . Wiley-VCH; Weinheim: 2012
• 8d Narula AP. S. Chem. Biodiversity 2004; 1: 1992
• 8e Frater G, Bajgrowicz JA, Kraft P. Tetrahedron 1998; 54: 7633
• 9a Modern Gold Catalyzed Synthesis . Hashmi AS. K, Toste FD. Wiley-VCH; Weinheim: 2012
• 9b Gold Catalysis: An Homogeneous Approach . Toste FD, Michelet V. Imperial College Press; London: 2014
• 9c The Chemistry of Organogold Compounds. In Patai’s Chemistry of Functional Groups. Rappoport Z, Liebman JF, Marek I. Wiley; Hoboken: 2014
• 9d Homogeneous Gold Catalysis. In Topics in Current Chemistry. Slaughter LM. Springer; Berlin: 2015
• 9e Brill M, Nolan SP. Top. Organomet. Chem. 2015; 62: 51
• 9f Bugoni S, Merlini V, Porta A, Gaillard S, Zanoni G, Nolan SP, Vidari G. Chem. Eur. J. 2015; 21: 14068
• 9g Merlini V, Gaillard S, Porta A, Zanoni G, Vidari G, Nolan SP. Tetrahedron Lett. 2011; 52: 1124
• 10a Fürstner A, Schlecker A. Chem. Eur. J. 2008; 14: 9181
• 10b Fehr C, Vuagnoux M, Buzas A, Arpagaus J, Sommer H. Chem. Eur. J. 2011; 17: 6214
• 10c Mamane V, Gress T, Krause H, Fürstner A. J. Am. Chem. Soc. 2004; 126: 8654
• 10d Harrak Y, Blaszykowski C, Bernard M, Cariou K, Mainetti E, Mouriès V, Dhimane A.-L, Fensterbank L, Malacria M. J. Am. Chem. Soc. 2004; 126: 8656
• 11a Arcadi A, Chiarini M, Del Vecchio L, Marinelli F, Michelet V. Eur. J. Org. Chem. 2017; 2214
• 11b Tomas-Mendivil E, Heinrich C, Ortuno J.-C, Starck J, Michelet V. ACS Catal. 2017; 7: 380
• 11c Arcadi A, Chiarini M, Del Vecchio L, Marinelli F, Michelet V. Chem. Commun. 2016; 52: 1458
• 11d Arcadi A, Pietropaolo E, Alvino A, Michelet V. Org. Lett. 2013; 15: 2766
• 11e Mariaule G, Newsome G, Toullec PY, Belmont P, Michelet V. Org. Lett. 2014; 16: 4570
• 11f Tang Y, Benaissa I, Huynh M, Vendier L, Lugan N, Bastin S, Belmont P, César V, Michelet V. Angew. Chem. Int. Ed. 2019; 58: 7977
• 11g Chen X, Martini S, Michelet V. Adv. Synth. Catal. 2019; 361: 3612
• 11h Heinrich CF, Durand D, Starck J, Michelet V. Org. Lett. 2020; 22: 7064
• 11i Davenel V, Nisole C, Fontaine-Vive F, Fourquez J.-M, Chollet A.-M, Michelet V. J. Org. Chem. 2020; 85: 12657
• 12 Laher R, Marin C, Michelet V. Org. Lett. 2020; 22: 4058
• 13 Ye L, Chen Q, Zhang J, Michelet V. J. Org. Chem. 2009; 74: 9550
• 14 Renner H, Schlamp G, Hollmann D, Lüschow HM, Tews P, Rothaut J, Dermann K, Knödler A, Hecht C, Schlott M, Drieselmann R, Peter C, Schiele R. Gold, Gold Alloys, and Gold Compounds . In Ullmann’s Encyclopedia of Industrial Chemistry . Wiley-VCH; Weinheim: 2000: a12_49
• 15a www.thegoodscentscompany.com/data/rw1015272.html
• 15b Demole E, Lederer E, Mercier D. Helv. Chim. Acta 1962; 45: 675
• 15c Chapuis C. Helv. Chim. Acta 2012; 95: 1479
• 15d Chapuis C, Skuy D, Richard CA. Chimia 2019; 73: 194
• 16a Krafft ME, Scott IL, Romero RH, Feibelmann S, Van Pelt CE. J. Am. Chem. Soc. 1993; 115: 7199
• 16b Morimoto T, Fuji K, Tsutsumi K, Kakiuchi K. J. Am. Chem. Soc. 2002; 124: 3806
• 16c Harrak Y, Simonneau A, Malacria M, Gandon V, Fensterbank L. Chem. Commun. 2010; 46: 865
• 16d Diao Y, Zuo Z, Wang H, Liu J, Luan X. Org. Biomol. Chem. 2017; 15: 4601
• 16e Barbazanges M, Auge M, Moussa J, Amouri H, Aubert C, Desmarets C, Fensterbank L, Gandon V, Malacria M, Ollivier C. Chem. Eur. J. 2011; 17: 13789
• 16f Nieto-Oberhuber C, Perez-Galan P, Herrero-Gomez E, Lauterbach T, Rodriguez C, Lopez S, Bour C, Rosellon A, Cardenas DJ, Echavarren AM. J. Am. Chem. Soc. 2008; 130: 269
• 16g Laird T, Ollis WD, Sutherland IO. J. Chem. Soc., Perkin Trans. 1 1980; 1473
• 16h Terada A, Kishida Y. Chem. Pharm. Bull. 1969; 17: 966
• 17a Shibata T, Kobayashi Y, Maekawa S, Toshida N, Takagi K. Tetrahedron 2005; 61: 9018
• 17b Blum J, Beer-Kraft H, Badrieh Y. J. Org. Chem. 1995; 60: 5567
• 18a Erkkilä A, Pihko PM. Eur. J. Org. Chem. 2007; 4205
• 18b Danheiser RL, Nowick JS. J. Org. Chem. 1991; 56: 1176
• 18c Grigg R, Scott R, Stevenson P. J. Chem. Soc., Perkin Trans. 1 1988; 1365
• 18d Cao X.-P, Chan T.-L, Chow H.-F. Tetrahedron Lett. 1996; 37: 1049