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Synthesis 2018; 50(23): 4606-4610
DOI: 10.1055/s-0037-1610659
DOI: 10.1055/s-0037-1610659
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Preparation of Rearranged Allylic Isocyanates from the Reaction of Allylic Alcohols with 1-Cyano-4-dimethylaminopyridinium Bromide
We are grateful to the following agencies for financial support of this work: Natural Sciences and Engineering Research Council of Canada (NSERC) (Idea to Innovation and Discovery Grants), Canada Research Chair Program, Canada Foundation for Innovation (CFI), TDC Research, Inc., TDC Research Foundation, the Ontario Partnership for Innovation and Commercialization (OPIC), and The Advanced Biomanufacturing Centre (Brock University).Further Information
Publication History
Received: 14 July 2018
Accepted after revision: 05 September 2018
Publication Date:
11 October 2018 (online)
Abstract
A shorter and less costly alternative to Ichikawa’s [1,3]-transposition protocol for cyanates to isocyanates is described.
Key words
sigmatropic rearrangement - [1,3]-transposition - allylic alcohol - methodology - total synthesisSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1610659.
- Supporting Information
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References
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For the related [3,3]-sigmatropic rearrangement of allylic thiocyanates see:
For other examples of [3,3]-sigmatropic rearrangements see:
For the discovery of this reaction, see:
For recent reviews in this field, see:
For the detailed experimental procedure, see:
For the stereochemistry of the reaction, see: