Rhenium-catalyzed regio- and stereoselective addition of two carbon units to terminal alkynes via carbon-carbon bond cleavage of β-keto sulfones

Organic Letters

Volumn 13, Issue 11, 2011, Pages 2959-2961

  Kuninobu, Yoichiro ^a   Matsuzaki, Hironori ^a   Nishi, Mitsumi ^a   Takai, Kazuhiko ^a  

^a OKAYAMA UNIVERSITY   (Japan)

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EID: 79957812665     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol2008507     Document Type: Article

References (25)

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20. 3.
21. 2Cl, 31%; DMF, 0%; ethanol, 0%; neat, 4%.
22. In this reaction, while p -tolylacetylene (2a) was consumed, β-keto sulfone 1a was recovered in 16% yield. However, the yield of the product 3a was not improved by treatment with additional alkyne 2a.
23. In Table 1, entries 1-8, β-keto sulfones 1 were recovered. The total yields of the products 3 and the recovery of β-keto sulfones 1 were between 84 and 98%. Therefore, the yields of 3 based on the conversion were relatively high.
24. The olefin configurations of other products were assigned by the comparison of the chemical shifts of the olefinic protons of the products with those of 3f.
25. In Table 2, entries 1-9, β-keto sulfones 1 were recovered. The total yields of the products 3 and the recovery of β-keto sulfones 1 were in the range 88-99%. Therefore, the yields of 3 based on the conversion were relatively high.