Journal
ADVANCED SYNTHESIS & CATALYSIS
Volume 352, Issue 10, Pages 1701-1710Publisher
WILEY-BLACKWELL
DOI: 10.1002/adsc.201000094
Keywords
alkynes; catalyst recovery; catalysis; enol ethers; gold; hydroalkoxylation
Categories
Funding
- Generalitat Valenciana
- MICINN
- Consejo Superior de Investigaciones Cientificas (CSIC)
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Vinyl ethers and ketals are obtained from the reaction of phenylacetylene derivatives and dimethyl acetylenedicarboxylate (DMAD) with alcohols in good yields and levels of stereoselectivity by using cationic gold(I)-phosphine complexes as catalysts. By choosing the appropriate phosphine, the selective formation of the Z or the E isomer of the vinyl ether can be tuned, and the undesired formation of the ketal can be controlled. The isomerisation of fumarates (Z-isomer) to maleates (E-isomer) is a gold-catalysed process that can be conducted in one-pot. When using polyols, 5-membered cyclic ketals are easily isolated by extraction with hexane and the gold complex can be reused.
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