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Synthesis 2020; 52(22): 3461-3465
DOI: 10.1055/s-0040-1707191
DOI: 10.1055/s-0040-1707191
paper
Efficient Synthesis of O-tert-Propargylic Oximes via Nicholas Reaction
Authors
This work was supported by JSPS KAKENHI Grant Number JP16H00996 in Precisely Designed Catalysts with Customized Scaffolding and JP20H02731 (Grant-in-Aid for Scientific Research (B)) from MEXT Japan.
Further Information
Publication History
Received: 26 May 2020
Accepted after revision: 09 June 2020
Publication Date:
21 July 2020 (online)
Abstract
A synthetic protocol to access O-tert-propargylic oximes derived from tertiary propargylic alcohols was established via Nicholas reaction. Thus, BF3·OEt2-mediated reaction between the dicobalt hexacarbonyl complex of tert-propargylic alcohols and p-nitrobenzaldoxime followed by decomplexation with cerium(IV) ammonium nitrate afforded the corresponding O-tert-propargylic oximes in good to high yields. The obtained O-tert-propargylic oximes were effectively converted into heterocycles, such as four-membered cyclic nitrones, oxazepines, and isoxazolines, by using π-Lewis acidic catalysts.
Key words
Nicholas reaction - alkynes - tertiary alcohols - heterocycles - gold catalysts - spirocyclesSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0040-1707191.
- Supporting Information (PDF) (opens in new window)
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