69939-72-6Relevant academic research and scientific papers
Transition-Metal-Free Synthesis of Electron Rich 1,3-Dienes via Base Promoted Isomerization of Propargylic Ethers
Liu, Chunxiang,Deng, Guogang,Li, Xin,Xu, Yiren,Yu, Kaili,Chen, Wen,Zhang, Hongbin,Yang, Xiaodong
, p. 483 - 487 (2020)
Herein, a novel and scalable synthesis of electron rich 1,3-dienes based on KOtBu mediated isomerization of propargylic ether derivatives was developed. This new process features easy handling reaction conditions, transition-metal-free isomerization, high isolated yields, and most of all, it could be used for modification of natural products at late stage functionalizations.
Cyclopropanation of Benzene Rings by Oxidatively Generated α-Oxo Gold Carbene: One-Pot Access to Tetrahydropyranone-Fused Cycloheptatrienes from Propargyl Benzyl Ethers
Ji, Kegong,Zhang, Liming
supporting information, p. 647 - 651 (2017/12/26)
Cyclopropanations of benzene rings by oxidatively generated α-oxo gold carbenes are for the first time demonstrated in a Buchner reaction, in which readily available propargyl benzyl ethers are converted in one-pot to tetrahydropyranone-fused cycloheptatrienes via sequential oxidative gold catalysis and base-promoted isomerization. Additional examples of arene cyclopropanations without fragmentation of the cyclopropane ring are also realized. (Figure presented.).
Platinum-catalyzed α,β-unsaturated carbene formation in the formal syntheses of frondosin B and liphagal
Huynh, Khoi Q.,Seizert, Curtis A.,Ozumerzifon, Tarik J.,Allegretti, Paul A.,Ferreira, Eric M.
supporting information, p. 294 - 297 (2017/11/28)
Formal syntheses of tetracyclic terpenoids frondosin B and liphagal are described. Both synthetic routes rely on the use of platinum-catalyzed α,β-unsaturated carbene formation for the key C-C bond forming transformations. The successful route toward frondosin B utilizes a formal (4 + 3) cycloaddition, while the liphagal synthesis features the vinylogous addition of an enol nucleophile as a key step. Both synthetic routes are discussed, revealing insights into structural requirements in the catalytic a,β-unsaturated carbene reaction manifold.
