When Gold Meets Perfumes: Synthesis of Olfactive Compounds via Gold-Catalyzed Cycloisomerization Reactions

被引：25

作者：

Laher, Romain ^{[1
]}

Marin, Christophe ^{[2
]}

Michelet, Veronique ^{[1
]}

机构：

[1] Univ Cote Azur, Inst Chim Nice, F-06108 Nice 2, France

[2] Express Parfumees, F-06130 Grasse, France

来源：

ORGANIC LETTERS | 2020年 / 22卷 / 11期

关键词：

DOMINO HYDROARYLATION/CYCLOISOMERIZATION REACTIONS; GOLD(I)-CATALYZED CYCLOISOMERIZATION; ENANTIOSELECTIVE CYCLOISOMERIZATION; UNPROTECTED; 2-ALKYNYLANILINES; OXIDATIVE CYCLIZATION; COMPLEXES; 1,6-ENYNES; ANIONS; ENTRY;

D O I：

10.1021/acs.orglett.0c00843

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient, and mild synthetic route for the preparation of functionalized volatile oxa-bicyclo[4.1.0]-hept-4-ene (29 compounds, 44-98% isolated yields) has been developed relying on the association of IPrAuCl with NaBArF. The remarkable selectivity was demonstrated on a 1 g and 25 g scale with low catalyst loadings. The synthetic utility of these low-molecular-weight enols was further demonstrated by the derivatization of some adducts and by the unprecedented olfactory evaluation of all bicyclic derivatives.

引用

页码：4058 / 4062

页数：5

共 66 条

[1] Phosphathiahelicenes: Synthesis and Uses in Enantioselective Gold Catalysis [J].

Aillard, Paul ;

Voituriez, Arnaud ;

Dova, Davide ;

Cauteruccio, Silvia ;

Licandro, Emanuela ;

Marinetti, Angela .

CHEMISTRY-A EUROPEAN JOURNAL, 2014, 20 (39) :12373-12376

[2] Silver-versus gold-catalyzed sequential oxidative cyclization of unprotected 2-alkynylanilines with oxone [J].

Arcadi, A. ;

Chiarini, M. ;

Del Vecchio, L. ;

Marinelli, F. ;

Michelet, V. .

CHEMICAL COMMUNICATIONS, 2016, 52 (07) :1458-1461

[3] Sequential Silver-Catalyzed Oxidative Cyclization Reactions of Unprotected 2-Alkynylanilines to Anthranils [J].

Arcadi, Antonio ;

Chiarini, Marco ;

Del Vecchio, Luana ;

Marinelli, Fabio ;

Michelet, Veronique .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2017, 2017 (16) :2214-2222

[4] One-Pot Gold-Catalyzed Aminofluorination of Unprotected 2-Alkynylanilines [J].

Arcadi, Antonio ;

Pietropaolo, Emanuela ;

Alvino, Antonello ;

Michelet, Veronique .

ORGANIC LETTERS, 2013, 15 (11) :2766-2769

[5]

Bajgrowicz J. A., 1997, European Patent, Patent No. 0801049

[6] Atropisomeric [(diphosphine)Au2Cl2] Complexes and their Catalytic Activity Towards Asymmetric Cycloisomerisation of 1,6-Enynes [J].

Barreiro, Elena M. ;

Boltukhina, Ekaterina V. ;

White, Andrew J. P. ;

Hii, King Kuok .

CHEMISTRY-A EUROPEAN JOURNAL, 2015, 21 (06) :2686-2690

[7] Acidic Co-Catalysts in Cationic Gold Catalysis [J].

Barrio, Pablo ;

Kumar, Manish ;

Lu, Zhichao ;

Han, Junbin ;

Xu, Bo ;

Hammond, Gerald B. .

CHEMISTRY-A EUROPEAN JOURNAL, 2016, 22 (46) :16410-16414

[8] A NOVEL PTCL4-CATALYZED CYCLOREARRANGEMENT OF ALLYL PROPYNYL ETHERS TO 3-OXABICYCLO[4.1.0]HEPTENES [J].

BLUM, J ;

BEERKRAFT, H ;

BADRIEH, Y .

JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (17) :5567-5569

[9]

Bontemps A, 2016, SYNTHESIS-STUTTGART, V48, P2178, DOI 10.1055/s-0035-1562234

[10] Heterogeneous gold-catalysed synthesis of phenols [J].

Carrettin, Silvio ;

Blanco, M. Carmen ;

Corma, Avelino ;

Hashmi, A. Stephen K. .

ADVANCED SYNTHESIS & CATALYSIS, 2006, 348 (10-11) :1283-1288

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