178323-48-3Relevant academic research and scientific papers
Regio- and stereoselective heck α-arylation of cinnamyl alcohols
Ambrogio, Ilaria,Cacchi, Sandro,Fabrizi, Giancarlo,Goggiamani, Antonella,Sgalla, Simona
scheme or table, p. 620 - 624 (2009/07/11)
The Heck reaction of cinnamyl alcohols with aryl iodides has been investigated using n-Bu4NOAc as the base in toluene. Under these conditions, the reaction affords regio- and stereoselectively (Z)-2,3-diarylallylic alcohols in moderate to good yields. Experimental evidence suggests that the observed selectivity in formation of the vinylic substitution products is kinetic in origin under these conditions and that both the base and the solvent play a key role. Georg Thieme Verlag Stuttgart.
New synthesis of isoxazolidines
Malamas, Michael S.,Palka, Cynthia L.
, p. 475 - 478 (2007/10/03)
A new synthesis of 5-substituted isoxazolidines was developed by direct isoxazolidine ring formation of allylic hydroxylamines under acidic conditions. The cyclization process is an electrophilic SN1 type reaction. The formed carbocation intermediate is stabilized by electron rich groups (i.e., phenyl). A moiety that mediates oxonium ion formation (i.e., para-methoxy) accelerates the rate of product formation.
