Unravelling the nucleophilicity of buten tides for 1,6-conjugate addition to p-quinone methides: a direct access to diversely substituted butenolide-derived diarylmethanes
| Title | Unravelling the nucleophilicity of buten tides for 1,6-conjugate addition to p-quinone methides: a direct access to diversely substituted butenolide-derived diarylmethanes |
| Publication Type | Journal Article |
| Year of Publication | 2018 |
| Authors | Sharma, BM, Shinde, DR, Jain, R, Begari, E, Satbhaiya, S, Gonnade, RG, Kumar, P |
| Journal | Organic Letters |
| Volume | 20 |
| Issue | 9 |
| Pagination | 2787-2791 |
| Date Published | MAY |
| Abstract | A Lewis acid catalyzed regioselective C-C bond is constructed through beta-addition of deconjugated butenolides with p-quinone methides in a 1,6-conjugate addition manner. Interestingly, Lewis acid catalyzed vinylogous Mukaiyama-Michael reaction of silyloxyfurans with p-QMs proceeds selectively through the alpha or gamma position exclusively. The reaction is mild with broad substrate scope, thus allowing easy access to a wide range of bis-arylated alpha-/beta-/gamma-substituted butenolides. |
| DOI | 10.1021/acs.orglett.8b00745 |
| Type of Journal (Indian or Foreign) | Foreign |
| Impact Factor (IF) | 6.579 |
Divison category:
Central NMR Facility
Organic Chemistry
Physical and Materials Chemistry
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