Abstract
An efficient organocatalytic cascade reaction for the synthesis of the bicyclo[3.3.1]nonan-9-one skeleton is reported. The cascade reaction proceeds smoothly between prochiral 4-substituted cyclohexanones and (E)-2-(3-arylallylidene)-indene-1,3-diones involving a 1,6-/γ-protonation/1,4-addition sequence to construct bicyclic products that contain five stereogenic centers in good to high chemical yields and excellent diastereo- and enantioselectivity (up to >20:1 dr and 97% ee) in the presence of a thioether-linked l-prolinol-camphor-derived organocatalyst at ambient temperature. An interesting organocatalytic three-component triple cascade reaction has been performed to produce a bicyclo[2.2.2]octan-2-one in a favorable chemical yield and stereoselectivity (>19:1 dr and 97% ee) starting from 1,3-indanedione, an enal, and cyclohexenone in the presence of a primary amine organocatalyst. (Figure presented.).
Original language | English |
---|---|
Pages (from-to) | 3005-3013 |
Number of pages | 9 |
Journal | Advanced Synthesis and Catalysis |
Volume | 359 |
Issue number | 17 |
DOIs | |
Publication status | Published - 2017 Sep 4 |
Keywords
- bicyclic compounds
- cascade reaction
- enantioselectivity
- organocatalysis
- vinylogous process
ASJC Scopus subject areas
- Catalysis
- Organic Chemistry