5497-67-6Relevant articles and documents
Synthesis of 2,5-difunctionalised-3,3-dimethylpiperidines via ω-halogenated imines
Stevens, Christian V,Peristeropoulou, Maria,De Kimpe, Norbert
, p. 7865 - 7870 (2001)
2,5-Difunctionalised-3,3-dimethylpiperidines were prepared by addition of nucleophiles to piperideinium salts, formed by electrophile-induced cyclisation of γ,δ-unsaturated imines with N-bromosuccinimide in alcoholic medium.
Consecutive borylcupration/C-C coupling of ?-alkenyl aldehydes towards diastereoselective 2-(borylmethyl)cycloalkanols
Carbó, Jorge J.,Fernández, Elena,Maza, Ricardo J.,Royes, Jordi
supporting information, p. 5973 - 5976 (2020/06/05)
Copper(i) catalyzes the borylative cyclization of ?-alkenyl aldehydes through chemo- and regioselective addition of Cu-B to C?C and concomitant intramolecular 1,2-addition of Cu-C on C?O. The products are formed in an exclusive diastereoselective manner and computational analysis identifies the key points for the observed chemo- and diastereoselectivity.
A One-Pot Intramolecular Tandem Michael-Aldol Annulation Reaction for the Synthesis of Chiral Pentacyclic Terpenes
Lu, Jianyu,Koldas, Serkan,Fan, Huafang,Desper, John,Day, Victor W.,Hua, Duy H.
, p. 3964 - 3972 (2019/10/28)
A chiral tricyclic terpene possessing a 6,6,6-tricyclic framework and a 3,3-dimethyl-7-oxooctylidenyl side chain undergoes a double ring-closing reaction to give two chiral pentacyclic terpenes in a ratio of 4:3 via an intramolecular Michael addition followed by aldol condensation under basic conditions. Three new stereogenic centers are introduced in the initial Michael annulation reaction. Stereoselective installation of an ethoxycarbonyl group at C17 of the two pentacyclic terpenes separately gives the corresponding highly functionalized pentacyclic terpenoids with seven stereogenic centers. The structures and stereochemistry of key intermediates and products are established through X-ray crystallographic analysis. A mechanism is proposed for explaining the stereochemistry in the Michael annulation reaction.
Synthesis of a biofuel target through conventional organic chemistry
Page, Jordan P.,Robinson, Joshua W.,Albrecht, Karl O.,Cosimbescu, Lelia
supporting information, p. 1421 - 1423 (2018/03/07)
In this work, the biofuel target compound 2-ethyl-5,5-dimethylcyclopenta-1,3-diene (1) and its exo isomers (9a and 9b), were successfully synthesized via two different pathways from the common intermediate 4,4-dimethylcyclopent-2-ene-1-one (2). The first pathway produced the endocyclic product as a pure isomer via a triflate intermediate obtained from ketone 2 in 60% yield, followed by copper-catalyzed coupling with ethyl magnesium bromide in 63% yield. The second pathway employed a Grignard reaction with ketone 2, which generated an alcohol that was immediately subjected to mild acid-catalyzed elimination to yield primarily a mixture of exo isomers 9a and 9b in 46% yield. The preparation method developed by this work allowed for the production of a sufficient quantity of these targets to evaluate their fuel properties, which will be reported in a separate study.