Journal
ORGANIC LETTERS
Volume 13, Issue 5, Pages 1064-1067Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol103110q
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Funding
- National Natural Science Fundation of China [20903042]
- Program for new Century Excellent Talents in the University of China [NCET-10-0383]
- Hubei provincial government
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An electrophilic ring-opening reaction of 2-alkoxy-3,4-dihydropyran with a thiophenol or thiol is developed for the first time. The generated product contains not only a 1,3-dicarbonyl moiety but also a fragment of bis(alkylthio)methane. A possible mechanism is also proposed on the basis of postulating a ring-opening monotransthioacetalization product, which was prepared by using LiBr as catalyst as an intermediate.
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