Stereochemical Control by an Ester Group or Olefin Ligand in Platinum‐Catalyzed Carboalkoxylation of 6‐(1‐Alkoxyethoxy)‐ hex‐2‐ynoates
摘要：
The cyclization of 6-(1-alkoxyethoxy)hex-2-ynoantes in the presence of the platinum-olefin catalyst system gave the corresponding multisubstituted 2-[dihydrofuran-2( 3H )-ylidene]acetates in good to high yields. The Z/E selectivity is controlled by the electronic property of the ester group; the 2,2,2-trichloroethyl ester yielded the Z isomer, while the phenyl ester gave the E isomer. Moreover, we found that the Z/E selectivities in the reaction of phenyl esters 1h, 1n , and 1o were controlled by the olefin ligand. For example, the platinum-catalyzed reaction of 1h using 1,5-hexadiene as the olefin ligand gave E - 2h as the major product, while that using 1,5-cyclooctadiene produced mainly the Z isomer.
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DOI：
10.1002/adsc.200800772
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年份：
2010
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