Mondal, Santigopal ; Mukherjee, Subrata ; Yetra, Santhivardhana Reddy ; Gonnade, Rajesh G. ; Biju, Akkattu T. (2017) Organocatalytic Enantioselective Vinylogous Michael-Aldol Cascade for the Synthesis of Spirocyclic Compounds Organic Letters, 19 (16). pp. 4367-4370. ISSN 1523-7060
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Official URL: http://doi.org/10.1021/acs.orglett.7b02085
Related URL: http://dx.doi.org/10.1021/acs.orglett.7b02085
Abstract
Enantioselective synthesis of pyrazolone-fused spirocyclohexenols by the secondary amine-catalyzed cascade reaction of α,β-unsaturated aldehydes with α-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 α,β-unsaturated iminium ions from enals and tandem dienolate/enolate formation from pyrazolinones are the key for the success of this spiroannulation reaction.
Item Type: | Article |
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Source: | Copyright of this article belongs to American Chemical Society |
ID Code: | 128641 |
Deposited On: | 03 Nov 2022 06:50 |
Last Modified: | 03 Nov 2022 06:50 |
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