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Unexpected Formation of a Chiral spiro‐system in the Reaction of the Dilithium Derivative of Hexafluorocumyl Alcohol with N‐(t–butylsulfenyl)phthalimide
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Unexpected Formation of a Chiral spiro‐system in the Reaction of the Dilithium Derivative of Hexafluorocumyl Alcohol with N‐(t–butylsulfenyl)phthalimide
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Unexpected Formation of a Chiral spiro‐system in the Reaction of the Dilithium Derivative of Hexafluorocumyl Alcohol with N‐(t–butylsulfenyl)phthalimide
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Journal Article
Unexpected Formation of a Chiral spiro‐system in the Reaction of the Dilithium Derivative of Hexafluorocumyl Alcohol with N‐(t–butylsulfenyl)phthalimide
2025
Overview
An unexpected course of the reaction of hexafluorocumyl alcohol dilithium derivative 2 with N‐(t‐butylsulfenyl)phthalimide (3) has been presented. The process proceeded under mild conditions and resulted in previously undescribed chiral spiro‐system‐ 3′,3′‐bis(trifluoromethyl)‐3H,3′H‐1,1′‐spirobis(isobenzofuran)‐3‐one (5) as the only product. A detailed spectral analysis of the product has been provided, and mechanistic aspects have been investigated. Attempts to separate the enantiomers of compound 5 using a semipreparative HPLC method with a chiral stationary phase column have been described. The repeatability of the reaction using analogs of alcohol 4 has also been tested. DFT calculations of absolute configuration assignment have been performed successfully. The reaction of the hexafluorocumyl alcohol dilithium derivative with N‐(t‐butylsulfenyl)phthalimide unexpectedly resulted in the formation of a chiral spiro compound, which was fully characterized employing spectroscopic, chromatographic, and crystallographic analyses, as well as DFT calculations. A theoretical mechanism of the reaction was proposed. The versatility of the reaction was tested.
