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Regioselective Functionalization of Ester‑, Amide‑, Carbonate‑, and Carbamate-Substituted 2‑Phenyl-2-oxazolines with Mixed Lithium–Magnesium Amides
We have prepared novel highly functionalized benzene derivatives by regioselective metalation of ester-, amide-, carbamate-, and carbonate-substituted 2-phenyl-2-oxazolines with mixed lithium–magnesium amides followed by reaction with different electrophiles. While a complementary metalation site ca...
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| Published in: | Journal of organic chemistry 2021-01, Vol.86 (1), p.1204-1215 |
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| Main Authors: | , , , , , |
| Format: | Article |
| Language: | English |
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| cited_by | cdi_FETCH-LOGICAL-a333t-83ae07ff4b5d32731a30ce5495bc57d3ba2e7640819307f55b68a0db395edd83 |
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| cites | cdi_FETCH-LOGICAL-a333t-83ae07ff4b5d32731a30ce5495bc57d3ba2e7640819307f55b68a0db395edd83 |
| container_end_page | 1215 |
| container_issue | 1 |
| container_start_page | 1204 |
| container_title | Journal of organic chemistry |
| container_volume | 86 |
| creator | Bozzini, Leandro A Santos, Thiago dos Murie, Valter E de Mello, Murilo B. M Vessecchi, Ricardo Clososki, Giuliano C |
| description | We have prepared novel highly functionalized benzene derivatives by regioselective metalation of ester-, amide-, carbamate-, and carbonate-substituted 2-phenyl-2-oxazolines with mixed lithium–magnesium amides followed by reaction with different electrophiles. While a complementary metalation site can be accessed by using different bases, steric and electronic effects promoted by the aromatic ring substituents also play an important role in reaction regioselectivity. Computational calculations of the aromatic hydrogen pK a values have helped us to rationalize the metalation preference by the complex-induced proximity effect concept. |
| doi_str_mv | 10.1021/acs.joc.0c02369 |
| format | article |
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| ispartof | Journal of organic chemistry, 2021-01, Vol.86 (1), p.1204-1215 |
| issn | 0022-3263 1520-6904 |
| language | eng |
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| source | American Chemical Society:Jisc Collections:American Chemical Society Read & Publish Agreement 2022-2024 (Reading list) |
| title | Regioselective Functionalization of Ester‑, Amide‑, Carbonate‑, and Carbamate-Substituted 2‑Phenyl-2-oxazolines with Mixed Lithium–Magnesium Amides |
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