CAS 1006613-82-6, Cat. No EN300-33271366
Reagent cyclopropanone surrogate
1-(Phenylsulfonyl)cyclopropanol is a bench-stable cyclopropanone surrogate that serves as a highly reactive reagent for the synthesis of tertiary cyclopropanols1,2. It is used as an in situ source of cyclopropanone, undergoing nucleophilic addition with a wide range of organometallic reagents (sp, sp2, and sp3 hybridized) to provide structurally diverse cyclopropanols, including enantioenriched variants with high diastereoselectivity. The reaction tolerates various substitution patterns and operates under mild conditions, with optimized procedures minimizing side products. 1-(Phenylsulfonyl)cyclopropanol plays a key role in the silver-catalyzed oxidative deconstruction of cyclopropanone hemiaminals. It serves as a precursor to β-fluorinated amides through a two-step, one-pot reaction with good yield and diastereoselectivity3.
Synonyms: 1-(benzenesulfonyl)cyclopropan-1-ol; ((1-hydroxycyclopropyl)sulfonyl)benzene; 1-(phenylsulfonyl)-1-cyclopropanol; 1-phenylsulfonylcyclopropanol
Selected publications
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General Synthesis of Cyclopropanols via Organometallic Addition to 1-Sulfonylcyclopropanols as Cyclopropanone Precursors.
Rivera, R. M.; Jang, Y.; Poteat, C. M.; Lindsay, V. N. G. Org Lett 2020, 22 (16), 6510–6515. DOI: 10.1021/acs.orglett.0c02303
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1‐(Phenylsulfonyl)Cyclopropanol.
Lindsay, V. N. G. Encyclopedia of Reagents for Organic Synthesis 2025, 1–3. DOI: 10.1002/047084289X.rn02563
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Divergent Synthesis of β-Fluoroamides via Silver-Catalyzed Oxidative Deconstruction of Cyclopropanone Hemiaminals.
Jang, Y.; Deng, W.; Sprague, I. S.; Lindsay, V. N. G. Org Lett 2023, 25 (28), 5389–5394. DOI: 10.1021/acs.orglett.3c01992