76643-90-8Relevant academic research and scientific papers
General switch in regioselectivity in the Mukaiyama aldol reaction of silyloxyfuran with aldehydes in aqueous solvents
Woyciechowska, Marta,Forcher, Gwenael,Buda, Szymon,Mlynarski, Jacek
supporting information, p. 11029 - 11031 (2013/01/15)
An unexpected yet disciplined course of catalytic Mukaiyama-aldol reaction instead of the expected vinylogous Mukaiyama-aldol reaction has been observed for the reaction of silyloxyfuran with various aldehydes under Lewis acid catalytic control in water-containing solvents.
Syntheis of 3-(1-Hydroxyalkyl)-5H-furan-2-ones: Study of their Reaction with Halogens
Calderon, Angel,March, Pedro de,Arrad, Mustafa el,Font, Josep
, p. 4201 - 4214 (2007/10/02)
The syntheis of 3-(1-hydroxyalkyl)-5H-furan-2-ones, 4a-c, is reported.The reaction of lactones 4a and 4b with bromine under typical ionic bromination conditions gives as major product the unexpected substitution of the allylic hydroxyl group.Only the less hindered double bond in 4c gives some proportion of the normal addition product.The bromine chloride addition to 4c proceeds with 55 percent yield, while lactone 4a does not add BrCl.All these results point to the fact that halogen addition to the double bond of 4 suffers at least from steric hindrance.Key words: 3-(1-hydroxyalkyl)-5H-furna-2-ones; bromination; bromine chlorination
