Abstract
An interesting organocatalytic reaction between 2-arylideneindane-1,3- diones and aldehydes has been developed that gives fully substituted cyclohexanes that bear two all-carbon quaternary centers. The dispirocyclohexanes were obtained in reasonable-to-good chemical yields and with high stereoselectivities (>95:5 d.r. and up to 99% ee) using a catalytic amount of commercially available α,α-l-diphenylprolinol trimethylsilyl ether (5 mol %) and DABCO (20 mol %) in DMF at -20 °C. The reaction proceeds through a unique Michael/Michael/aldol reaction that requires 2 equiv of the 2-arylideneindane-1,3-dione.
Original language | English |
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Pages (from-to) | 2880-2883 |
Number of pages | 4 |
Journal | Organic Letters |
Volume | 15 |
Issue number | 11 |
DOIs | |
Publication status | Published - 2013 Jun 7 |
ASJC Scopus subject areas
- Biochemistry
- Physical and Theoretical Chemistry
- Organic Chemistry