Copper-catalyzed asymmetric propargylic substitution with salicylaldehyde-derived imine esters

Copper-catalyzed asymmetric propargylic substitution with salicylaldehyde-derived imine esters and propargylic carbonates has been successfully realized, generating a wide range of chiral amino acid derivatives containing propargylic groups with excellent results (up to 95% yield and 94% ee). The or...

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Published inChemical communications (Cambridge, England) Vol. 58; no. 61; pp. 8552 - 8555
Main Authors Wang, Ruo-Qing, Shen, Chong, Cheng, Xiang, Dong, Xiu-Qin, Wang, Chun-Jiang
Format Journal Article
LanguageEnglish
Published Cambridge Royal Society of Chemistry 28.07.2022
Subjects
Amino acids
Asymmetry
Carbonates
Copper
Esters
Hydrogen bonds
Hydroxyl groups
Substitutes
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Summary:Copper-catalyzed asymmetric propargylic substitution with salicylaldehyde-derived imine esters and propargylic carbonates has been successfully realized, generating a wide range of chiral amino acid derivatives containing propargylic groups with excellent results (up to 95% yield and 94% ee). The ortho -hydroxy group of the salicylaldehyde-derived imine esters is crucial to increase the reactivity and stabilize the azomethine ylide, which may be due to the formation of an intramolecular hydrogen bond between the hydroxyl group and the imine group. A series of synthetic transformations were carried out to access other important chiral compounds, which displayed the synthetic versatility. Cu-catalyzed asymmetric propargylic substitution with salicylaldehyde-derived imine esters was successfully realized, generating a series of chiral amino acid derivatives containing propargylic groups with excellent results.
Bibliography:Electronic supplementary information (ESI) available: Experimental procedures, and NMR spectra of the compounds. See DOI
https://doi.org/10.1039/d2cc01695h
ObjectType-Article-1
SourceType-Scholarly Journals-1
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content type line 23
ISSN:1359-7345
1364-548X
DOI:10.1039/d2cc01695h