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Synthesis 2022; 54(19): 4210-4219
DOI: 10.1055/a-1811-8075
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Enantioselective Dearomative Alkynylation of Chromanones: Opportunities and Obstacles

Yong Guan
a   Worcester Polytechnic Institute, Worcester, MA 01609, USA
,
Tadas Buivydas
a   Worcester Polytechnic Institute, Worcester, MA 01609, USA
,
Remy F. Lalisse
b   The Ohio State University, Columbus, OH 43210, USA
,
Rameez Ali
a   Worcester Polytechnic Institute, Worcester, MA 01609, USA
,
Christopher M. Hadad
b   The Ohio State University, Columbus, OH 43210, USA
,
Anita E. Mattson  ∗
a   Worcester Polytechnic Institute, Worcester, MA 01609, USA
› Author AffiliationsWe gratefully acknowledge the National Institutes of Health for funding these studies through 1R35GM124804-01.
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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.

Key words

tertiary ether stereocenter - benzopyrylium triflate - bis(oxaolines) - alkynes - copper

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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