3810-26-2Relevant articles and documents
A unified approach to sesquiterpenes sharing trimethyl(p-tolyl) cyclopentanes: Formal total synthesis of (±)-laurokamurene B
Das, Mrinal K.,Dinda, Bidyut K.,Bisai, Vishnumaya
, p. 2039 - 2042 (2019)
A unified approach to the sesquiterpenoids sharing common trimethyl(p-tolyl) cyclopentane skeleton has been disclosed via a key Stork-Danheiser sequence on a cyclopentane based vinylogous ester with aryl Grignard reagent followed by α-methylation strategy
Synthesis of polysubstituted cyclopentenones via [4+1] reactions of TIPS-vinylketenes
Li, Zhi,Moser, William H.,Deng, Ruixue,Sun, Liangdong
, p. 10254 - 10257 (2007)
(Chemical Equation Presented) An efficient method for preparing a series of polysubstituted cyclopentenones from TIPS-vinylketenes and Koebrich reagent has been developed in this paper. Additionally, highly substituted cyclopentenones can be prepared via
Palladium-catalyzed intramolecular 5-endo-trig oxidative Heck cyclization: a facile pathway for the synthesis of some sesquiterpene precursors
Ray, Devalina,Paul, Sunanda,Brahma, Sulagna,Ray, Jayanta. K.
, p. 8005 - 8008 (2007)
An efficient and convenient method for the construction of substituted cyclopentenones via palladium-catalyzed intramolecular 5-endo-trig oxidative cyclization has been introduced as a powerful new strategy for the synthesis of sesquiterpenes.
Enantioselective Hydrogenation of Endocyclic Enones: the Solution to a Historical Problem?
Lang, Qiwei,Yang, Huaxin,Gu, Guoxian,Feng, Qiang,Wen, Jialin,Zhang, Xumu
supporting information, p. 933 - 936 (2021/03/03)
The enantioselective hydrogenation of endocyclic enones has been a historical problem for homogeneous catalysis. We herein report an efficient method to reduce endocyclic enones with molecular hydrogen. Catalyzed by a rhodium/Zhaophos complex, a variety of enones with five-, six- or seven-member ring were hydrogenated with high enantioselectivity (92%—99% ee). Excellent chemo- and enantioselectivity demonstrated this method was successfully applied in the enantioselective hydrogenation of citral to produce enantio-enriched citronellal.
Palladium-Catalyzed Cross-Coupling of Alkenyl Carboxylates
Becica, Joseph,Heath, Oliver R. J.,Leitch, David C.,Zheng, Cameron H. M.
supporting information, p. 17277 - 17281 (2020/07/31)
Carboxylate esters have many desirable features as electrophiles for catalytic cross-coupling: they are easy to access, robust during multistep synthesis, and mass-efficient in coupling reactions. Alkenyl carboxylates, a class of readily prepared non-aromatic electrophiles, remain difficult to functionalize through cross-coupling. We demonstrate that Pd catalysis is effective for coupling electron-deficient alkenyl carboxylates with arylboronic acids in the absence of base or oxidants. Furthermore, these reactions can proceed by two distinct mechanisms for C?O bond activation. A Pd0/II catalytic cycle is viable when using a Pd0 precatalyst, with turnover-limiting C?O oxidative addition; however, an alternative pathway that involves alkene carbopalladation and β-carboxyl elimination is proposed for PdII precatalysts. This work provides a clear path toward engaging myriad oxygen-based electrophiles in Pd-catalyzed cross-coupling.