Phatake, Ravindra S. ; Mullapudi, Venkannababu ; Wakchaure, Vivek C. ; Ramana, Chepuri V. (2017) Fluoride-mediated dephosphonylation of α-diazo-β-carbonyl phosphonates Organic Letters, 19 (2). pp. 372-375. ISSN 1523-7060
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Official URL: http://pubs.acs.org/doi/abs/10.1021/acs.orglett.6b...
Related URL: http://dx.doi.org/10.1021/acs.orglett.6b03573
Abstract
The possibility of fluoride-mediated selective dephosphonylation of α-diazo-β-carbonyl phosphonates such as the Ohira–Bestmann reagent has been proposed and executed. The resulting α-diazocarbonyl intermediates undergo a (3 + 2)-cycloaddition at room temperature with conjugated olefins and benzynes. Interestingly, under the current conditions, the resulting cycloaddition products underwent either N-acylation (with excess α-diazo-β-carbonyl phosphonates) or Michael addition (with conjugated olefins).
| Item Type: | Article |
|---|---|
| Source: | Copyright of this article belongs to American Chemical Society. |
| ID Code: | 105871 |
| Deposited On: | 01 Feb 2018 16:49 |
| Last Modified: | 01 Feb 2018 16:49 |
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