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Trifluoromethanesulfonic Acid‐Catalyzed Tandem Semi‐Pinacol Rearrangement/Alkyne‐Aldehyde Metathesis Reaction of Arylpropagylsulfonamide‐Tethered 2,3‐Epoxycyclohexan‐1‐ols to Spiropiperidines
Author(s) -
Lin MingNan,
Wu ShihHui,
Yeh MingChang P.
Publication year - 2011
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201100576
Subject(s) - chemistry , alkyne , aldehyde , pinacol , tandem , catalysis , metathesis , salt metathesis reaction , cascade reaction , combinatorial chemistry , organic chemistry , materials science , polymer , composite material , polymerization
A simple and efficient trifluoromethanesulfonic acid‐catalyzed cycloisomerization of arylpropagylsulfonamide‐tethered 2,3‐epoxycyclohexan‐1‐ols is described. The cyclization proceeds via tandem semi‐pinacol rearrangement/alkyne‐aldehyde metathesis to afford spiropiperidines under mild reaction conditions.