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.
Regio- and stereoselective heck α-arylation of cinnamyl alcohols / Ilaria, Ambrogio; Cacchi, Sandro; Fabrizi, Giancarlo; Goggiamani, Antonella; Simona, Sgalla. - In: SYNLETT. - ISSN 0936-5214. - 2009:4(2009), pp. 620-624. [10.1055/s-0028-1087912]
Regio- and stereoselective heck α-arylation of cinnamyl alcohols
CACCHI, Sandro;FABRIZI, Giancarlo;GOGGIAMANI, ANTONELLA;
2009
Abstract
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.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
