Diastereoselective synthesis of substituted cyclopentanones via [3 + 2] cycloaddition of sulfoxonium ylides with alkenes
- 1Department of Chemistry, Yale University 226 Prospect St. New Haven CT 06520 USA
Abstract
We report a straightforward one-step, highly diastereoselective [3 + 2] cycloaddition for the synthesis of cyclopentanones incorporating up to four stereogenic centres. Sulfoxonium ylides are readily available, safe-to-use reagents and were utilised as three-carbon synthons to introduce alkyl, aryl, and heteroatom substituents at the α-positions of the cyclopentanone. A variety of terminal and internal alkenes serve as two-carbon synthons for installation of alkyl, alkenyl, and (hetero)aryl substituents at the β-positions. Depending on the reactant combination, the cycloaddition is best performed either in hexafluoroisopropanol as the reaction solvent or with ZnCl2 as a Lewis acid in trifluoroethanol. Stereochemical analyses of the reaction products using trans- and cis-1,2-disubstituted alkenes support a stepwise cyclisation mechanism. The cyclopentanone products are versatile intermediates to other valuable compound classes such as diastereomerically pure δ-lactones and cyclopentanols.
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BibTeX
@article{yeo2026diastereoselective,
title = {{Diastereoselective synthesis of substituted cyclopentanones via [3 + 2] cycloaddition of sulfoxonium ylides with alkenes}},
author = {Jihyeon Yeo and Sebastian M. Krajewski and Jonathan A. Ellman},
journal = {Chemical Science},
year = {2026},
month = sep,
doi = {10.1039/d6sc05806j},
url = {https://doi.org/10.1039/d6sc05806j},
note = {CC BY 3.0},
}
RIS
TY - JOUR
TI - Diastereoselective synthesis of substituted cyclopentanones via [3 + 2] cycloaddition of sulfoxonium ylides with alkenes
AU - Jihyeon Yeo
AU - Sebastian M. Krajewski
AU - Jonathan A. Ellman
PY - 2026
DA - 2026/09/21
JO - Chemical Science
DO - 10.1039/d6sc05806j
UR - https://doi.org/10.1039/d6sc05806j
AB - We report a straightforward one-step, highly diastereoselective [3 + 2] cycloaddition for the synthesis of cyclopentanones incorporating up to four stereogenic centres. Sulfoxonium ylides are readily available, safe-to-use reagents and were utilised as three-carbon synthons to introduce alkyl, aryl, and heteroatom substituents at the α-positions of the cyclopentanone. A variety of terminal and internal alkenes serve as two-carbon synthons for installation of alkyl, alkenyl, and (hetero)aryl substituents at the β-positions. Depending on the reactant combination, the cycloaddition is best performed either in hexafluoroisopropanol as the reaction solvent or with ZnCl2 as a Lewis acid in trifluoroethanol. Stereochemical analyses of the reaction products using trans- and cis-1,2-disubstituted alkenes support a stepwise cyclisation mechanism. The cyclopentanone products are versatile intermediates to other valuable compound classes such as diastereomerically pure δ-lactones and cyclopentanols.
SN - 2041-6520
SN - 2041-6539
ER -