Journal
CHEMISTRY-AN ASIAN JOURNAL
Volume 13, Issue 17, Pages 2373-2377Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/asia.201800351
Keywords
[2+2] cycloaddition; boron Lewis acid; chiral BrOnsted acid catalyst; cyclobutane; phosphoric acid
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Funding
- JSPS KAKENHI [JP17H03054, JP15H05755, JP15H05810]
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BBr3-assisted chiral phosphoric acid catalysts for enantioselective [2+2] cycloaddition were developed. The reactions of phenyl vinyl sulfide with -substituted acroleins proceeded, and the corresponding [2+2] cycloadducts were obtained with high enantioselectivity. In particular, the [2+2] cycloadduct obtained from methacrolein is a synthetically useful optically active cyclobutane, which could be transformed to a key intermediate for (+)-frontalin, a pheromone of Asian elephants.
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