Use of a Semihollow-Shaped Triethynylphosphane Ligand for Efficient Formation of Six- and Seven-Membered Ring Ethers through Gold(I)-Catalyzed Cyclization of Hydroxy-Tethered Propargylic Esters
Use of a Semihollow-Shaped Triethynylphosphane Ligand for Efficient Formation of Six- and Seven-Membered Ring Ethers through Gold(I)-Catalyzed Cyclization of Hydroxy-Tethered Propargylic Esters
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DOI：
10.1002/adsc.201200949
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发表时间：
2013-03
影响因子：
5.4
通讯作者：
Hideto Ito;Ayumi Harada;H. Ohmiya;M. Sawamura
中科院分区：
文献类型：
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作者：
Hideto Ito;Ayumi Harada;H. Ohmiya;M. Sawamura
半空心三乙炔基膦配体的阳离子金（I）配合物有效地催化羟基炔丙酯形成六元和七元环醚。这种金催化表现出对伯，仲，叔醇底物与各种取代模式的反应的耐受性。以有用的产率获得了空间拥挤的2，2，6，6-四烷基取代的四氢吡喃衍生物以及6，6-和7，6-稠合双环二醚。此外，金催化剂适用于磺酰胺连接的炔丙酯反应，得到哌啶衍生物。
The formation of six- and seven-membered ring ethers from hydroxy-tethered propargylic esters was efficiently catalyzed by a cationic gold(I) complex with a semihollow-shaped triethynylphosphane ligand. This gold catalysis showed a tolerance toward the reactions of primary, secondary, and tertiary alcohol substrates with various substitution patterns. A sterically congested 2,2,6,6-tetraalkyl-substituted tetrahydropyran derivative as well as 6,6- and 7,6-fused bicyclic diethers were obtained in useful yields. In addition, the gold catalysis was applicable to the reaction of a sulfonamide-tethered propargylic ester to give a piperidine derivative.