103722-82-3Relevant academic research and scientific papers
Copper catalyzed regioselective coupling of allylic halides and alkynes promoted by weak inorganic bases
Bieber, Lothar W.,da Silva, Margarete F.
, p. 7088 - 7090 (2008/03/11)
Allylic halides and terminal alkynes couple under CuI catalysis in DMSO or DMF solution. In most cases, sodium carbonate or bicarbonate is sufficient to promote the reaction; less reactive alkynes require catalytic amounts of DBU. Bifunctional alkynes and halides can be reacted selectively according to the stoichiometry used. Trimethylsilyl, hydroxyl, ester and halide groups are tolerated in the alkyne. Most halides react without allylic rearrangement. The method is suitable for the synthesis of functionalized enynes.
INTRAMOLECULAR N-ALKENYLNITRONE-ADDITIONS. REGIO- AND STEREOCHEMISTRY
Oppolzer, W.,Siles, S.,Snowden, R. L.,Bakker, B. H.,Petrzilka, M.
, p. 3497 - 3509 (2007/10/02)
Efficient intramolecular cycloadditions of N-3-alkenyl- and N-4-alkenylnitrones proceed with opposite regioselection which is modified by dipolarophile-substituent effects.Polycyclic isoxazolidines are obtained in a highly stereocontrolled fashion, consistent with an endo-addition of the Z-nitrones.
