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Enantioselective Dearomative Alkynylation of Chromanones: Opportunities and Obstacles.

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.

SUBMITTER: Guan Y

PROVIDER: S-EPMC9897304 | biostudies-literature | 2022 Oct

REPOSITORIES: biostudies-literature

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Enantioselective Dearomative Alkynylation of Chromanones: Opportunities and Obstacles.

Guan Yong Y Buivydas Tadas T Lalisse Remy F RF Ali Rameez R Hadad Christopher C Mattson Anita E AE

Synthesis 20220609 19

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 ...[more]

PMID: 36744023

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