Base catalysed diastereoselective Tamura cycloaddition of vinylidene indanediones

[Display omitted] •Hünig’s base catalyses the Tamura cycloaddition of vinylidene indanedione.•The products spiro[indane-1,3-dione-1-tetralones] are formed in excellent yields.•Highly diasteroselective transformation under the conditions employed.•Chiral, bifunctional hydrogen bonding catalysts induc...

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Bibliographic Details
Published in:Tetrahedron letters 2019-01, Vol.60 (1), p.1-4
Main Authors: Donthi, Ravikiran, Reddy, Venkatram R., Reddy, Sivakumar N., Chandra, Rajesh
Format: Article
Language:English
Subjects:
Diastereoselective
Enantioselective
Organocatalysis
Tamura reaction
Vinylidene indanedione
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Summary:[Display omitted] •Hünig’s base catalyses the Tamura cycloaddition of vinylidene indanedione.•The products spiro[indane-1,3-dione-1-tetralones] are formed in excellent yields.•Highly diasteroselective transformation under the conditions employed.•Chiral, bifunctional hydrogen bonding catalysts induce moderate enantioselectivity. The base catalysed Tamura cycloaddition reaction of vinylidene indanediones afforded the corresponding spiro[indane-1,3-dione-1-tetralone] structures as single diastereomers in excellent yields. Chiral bifunctional hydrogen bonding thiourea catalysts rendered the reaction enantioselective. However, the selectivity observed was moderate with Soós catalyst providing an enantiomeric ratio of 82.5:17.5.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2018.10.074