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Synthesis 2022; 54(19): 4210-4219
DOI: 10.1055/a-1811-8075
DOI: 10.1055/a-1811-8075
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Enantioselective Dearomative Alkynylation of Chromanones: Opportunities and Obstacles
We gratefully acknowledge the National Institutes of Health for funding these studies through 1R35GM124804-01.
Abstract
A catalytic and highly enantioselective dearomative alkynylation of chromanones has been discovered that enables the construction of biologically relevant tertiary ether stereogenic centers. This methodology is robust, accommodating a variety of alkynes and chromanones. More than 40 substrates tested gave rise to >90% ee. Computational studies have indicated that the optimal indanyl ligand identified for most cases likely affords a network of supportive, non-covalent interactions that drive the enantioselective nature of the reaction.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-1811-8075.
- Supporting Information
Publication History
Received: 04 January 2022
Accepted after revision: 30 March 2022
Accepted Manuscript online:
30 March 2022
Article published online:
09 June 2022
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For select examples of enantioselective 2-alkylchromanone synthesis, see:
For select reports demonstrating the importance of constructing tertiary ether stereocenters from chromanones, see: