Bello Davide, O'Hagan David
University of St Andrews, School of Chemistry, North Haugh, St Andrews, Fife, KY16 9ST, UK.
Beilstein J Org Chem. 2015 Oct 14;11:1902-9. doi: 10.3762/bjoc.11.205. eCollection 2015.
A new method for the preparation of α-fluorovinyl thioethers is reported which involves the hydrofluorination of alkynyl sulfides with 3HF·Et3N, a process that requires Lewis acid activation using BF3·Et2O and TiF4. The method gives access to a range of α-fluorovinyl thioethers, some in high stereoselectivity with the Z-isomer predominating over the E-isomer. The α-fluorovinyl thioether motif has prospects as a steric and electronic mimetic of thioester enols and enolates, important intermediates in enzymatic C-C bond forming reactions. The method opens access to appropriate analogues for investigations in this direction.
报道了一种制备α-氟代乙烯基硫醚的新方法，该方法涉及用3HF·Et3N对炔基硫醚进行氢氟化，此过程需要使用BF3·Et2O和TiF4进行路易斯酸活化。该方法能够制备一系列α-氟代乙烯基硫醚，其中一些具有较高的立体选择性，Z-异构体比E-异构体占优势。α-氟代乙烯基硫醚基序有望作为硫酯烯醇和烯醇盐的空间和电子模拟物，而硫酯烯醇和烯醇盐是酶促C-C键形成反应中的重要中间体。该方法为朝这个方向的研究提供了合适的类似物。
