Organocatalytic enantioselective vinylogous michael-aidoi cascade for the synthesis of spirocyclic compounds
| Title | Organocatalytic enantioselective vinylogous michael-aidoi cascade for the synthesis of spirocyclic compounds |
| Publication Type | Journal Article |
| Year of Publication | 2017 |
| Authors | Mondal, S, Mukherjee, S, Yetra, SReddy, Gonnade, RG, Biju, AT |
| Journal | Organic Letters |
| Volume | 19 |
| Issue | 16 |
| Pagination | 4367-4370 |
| Date Published | AUG |
| Type of Article | Article |
| Abstract | Enantioselective synthesis of pyrazolone-fused spirocyclohexenols by the secondary amine-catalyzed cascade reaction of alpha,beta-unsaturated aldehydes with alpha-arylidene pyrazolinones is reported. This formal [3 + 3] organocascade reaction proceeds through a vinylogous Michael-aldol sequence to furnish the spiroheterocycles with three stereocenters including an all-carbon quaternary center in good yields and selectivities. The catalytic generation of alpha,beta-unsaturated iminium ions from enals and tandem dienolate/enolate formation from pyrazolinones are the key for the success of this spiroannulation reaction. |
| DOI | 10.1021/acs.orglett.7b02085 |
| Type of Journal (Indian or Foreign) | Foreign |
| Impact Factor (IF) | 6.732 |
Divison category:
Center for Material Characterization (CMC)
Organic Chemistry