Enantioselective Dearomative Alkynylation of Chromanones: Opportunities and Obstacles

Yong Guan; Tadas Buivydas; Remy F. Lalisse; Rameez Ali; Christopher M. Hadad; Anita E. Mattson

doi:10.1055/a-1811-8075

Synthesis, Table of Contents

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

^aWorcester Polytechnic Institute, Worcester, MA 01609, USA

,

Tadas Buivydas

^aWorcester Polytechnic Institute, Worcester, MA 01609, USA

,

Remy F. Lalisse

^bThe Ohio State University, Columbus, OH 43210, USA

,

Rameez Ali

^aWorcester Polytechnic Institute, Worcester, MA 01609, USA

,

Christopher M. Hadad

^bThe Ohio State University, Columbus, OH 43210, USA

,

Anita E. Mattson ∗

^aWorcester Polytechnic Institute, Worcester, MA 01609, USA

› Author Affiliations

Abstract

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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

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References

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