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

被引：24
|
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
收藏
页码：4058 / 4062
页数：5
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