Chelation-controlled intermolecular alkene and alkyne hydroacylation: the utility of beta-thioacetal aldehydes.
[reaction: see text]. Beta-thioacetal-substituted aldehydes, which are conveniently prepared from the corresponding ynals, can be combined with a range of alkynes or electron-poor alkenes to deliver intermolecular hydroacylation adducts. The reactions employ [Rh(dppe)]ClO4 as a catalyst and are proposed to proceed via a chelated rhodium acyl intermediate. The thioacetal-containing products can be deprotected to the corresponding ketones or reduced to alkanes in good yields.
Willis
Michael C
MC
Department of Chemistry, University of Bath, Bath, BA2 7AY, UK. m.c.willis@bath.ac.uk
Randell-Sly
Helen E
HE
Woodward
Robert L
RL
Currie
Gordon S
GS