Ramakrishna, Isai ; Grandhi, Gowri Sankar ; Sahoo, Harekrishna ; Baidya, Mahiuddin (2015) The Mukaiyama aldol reaction of in situ generated nitrosocarbonyl compounds: selective C–N bond formation and N–O bond cleavage in one-pot for α-amination of ketones Chemical Communications, 51 (73). pp. 13976-13979. ISSN 1359-7345
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Official URL: http://doi.org/10.1039/c5cc05459a
Related URL: http://dx.doi.org/10.1039/c5cc05459a
Abstract
A practical protocol for the α-amination of ketones (up to 99% yield) has been developed via the Mukaiyama aldol reaction of in situ generated nitrosocarbonyl compounds. The reaction with silyl enol ethers having a disilane (−SiMe2TMS) backbone proceeded not only with perfect N-selectivity but concomitant N–O bond cleavage was also accomplished. Such a cascade of C–N bond formation and N–O bond cleavage in a single step was heretofore unknown in the field of nitrosocarbonyl chemistry. A very high diastereoselectivity (dr = 19 : 1) was accomplished using (−)-menthol derived chiral nitrosocarbonyl compounds.
| Item Type: | Article |
|---|---|
| Source: | Copyright of this article belongs to Royal Society of Chemistry. |
| ID Code: | 131810 |
| Deposited On: | 08 Dec 2022 10:10 |
| Last Modified: | 08 Dec 2022 10:10 |
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