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Organocatalytic Atroposelective Hydrochalcogenation of Alkynes to Access Axially Chiral Vinyl Chalcogenides

16 August 2024, Version 1
Working Paper
This content is a preprint and has not undergone peer review at the time of posting.

Abstract

The low racemization barrier inherent in axially chiral vinyl sulfides/selenides (G ≤ 26.8 kcal/mol) poses a significant challenge for achieving atroposelective hydrochalcogenation of alkynes. In this study, we present an unprecedented atroposelective hydrochalcogenation of alkynes catalyzed by organocatalysts. This organocatalytic, atom-economic process proceeds under mild conditions and exhibits exceptional enantio-, regio-, and E-stereoselectivity. Insights from detailed Density Functional Theory (DFT) studies elucidate the origins of these high selectivities.

Keywords

alkyne
selenol
thiol
hydrochalcogenation
organocatalysis
atroposelectivity

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Version History

Aug 16, 2024 Version 1

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The content is available under CC BY NC ND 4.0 [opens in a new tab]

DOI

10.26434/chemrxiv-2024-z9crl
D O I: 10.26434/chemrxiv-2024-z9crl [opens in a new tab]

Funding

National Natural Science Foundation of China
No. 22201018
National Natural Science Foundation of China
No. 22371016
Beijing Natural Science Foundation
No.2222024
the National Key Research and Development Program of China
No.2021YFA1401200

Author’s competing interest statement

The author(s) have declared they have no conflict of interest with regard to this content

Ethics

The author(s) have declared ethics committee/IRB approval is not relevant to this content

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