Harnessing nucleophilicity of allenol ester with p-quinone methides via gold catalysis: application to the synthesis of diarylmethine-substituted enones
| Title | Harnessing nucleophilicity of allenol ester with p-quinone methides via gold catalysis: application to the synthesis of diarylmethine-substituted enones |
| Publication Type | Journal Article |
| Year of Publication | 2018 |
| Authors | Sharma, BM, Rathod, J, Gonnade, RG, Kumar, P |
| Journal | Journal of Organic Chemistry |
| Volume | 83 |
| Issue | 16 |
| Pagination | 9353-9363 |
| Date Published | AUG |
| Type of Article | Article |
| Abstract | A gold(I)-catalyzed protocol for intermolecular 1,6-conjugate addition of nucleophilic allenol ester generated in situ through [3,3]-sigmatropic rearrangement with p-quinone methides (p-QMs) has been developed. The gold catalyst plays a dual role by the pi-acid-triggered activation of alkynes and at the same time as a Lewis acid for activation of p-QMs toward nucleophilic attack. This method enables rapid access to a wide range of densely functionalized diarylmethine-substituted enones, a Morita-Baylis-Hillman (MBH) product with high selectivity, excellent yields, and broad substrate scope. |
| DOI | 10.1021/acs.joc.8b01294 |
| Type of Journal (Indian or Foreign) | Foreign |
| Impact Factor (IF) | 4.805 |
Divison category:
Organic Chemistry
Physical and Materials Chemistry
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