263720-75-8Relevant academic research and scientific papers
A direct and stereocontrolled route to conjugated enediynes
Jones, Graham B.,Wright, Justin M.,Plourde, Gary W.,Hynd, George,Huber, Robert S.,Mathews, Jude E.
, p. 1937 - 1944 (2000)
A unified synthetic route to 3-hex-en-1,5-diynes, a key building block found in many of the enediyne antitumor agents and designed materials, was developed. The method, which relies on a carbenoid coupling-elimination strategy is tolerant of a wide range of functionalities, and was applied to the synthesis of a variety of linear and cyclic enediynes. Reaction parameters can be adjusted to control stereoselectivity of the process, producing linear enediynes from 1:12 to >100:1 E:Z ratio, and in the case of cyclic enediynes, giving the exclusively Z C-9, C-10, or C-11 products. Key features of the process are the ready availability of precursors and the mildness and efficiency of the reaction. Application of the process in the design of materials precursors and preparation of enediyne antitumor agents are presented.
Highly Regioselective and E/ Z-Selective Hydroalkylation of Ynone, Ynoate, and Ynamide via Photoredox Mediated Ni/Ir Dual Catalysis
Go, Su Yong,Lee, Geun Seok,Hong, Soon Hyeok
, p. 4691 - 4694 (2018)
Exclusively α- and highly E/Z-selective hydroalkylation of ynone, ynoate, and ynamide was achieved via photoredox mediated Ni/Ir dual catalysis with high atom and step economy, producing trisubstituted enones, which are versatile synthetic building blocks. The developed reaction selectively delivered the α/Z isomer, which is complementary to the previously reported β-alkylation processes. The trisubstituted enones could be transformed to more valuable compounds via post-functionalization.
