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An appropriate solvent to perform the original Simmons–Smith reaction was reinvestigated. Among available solvents, cyclopentyl methyl ether (CPME), a recently commercialized ethereal solvent, was found to be the best so far. Compared with Et2O under reflux – the commonest conditions – reaction completion in CPME at 50 °C was about 10 times faster. The product yields and selectivities were mostly identical to those with Et2O, but were better in some cases; e.g. 13–56% with 2‐cyclohexenol. The good performance of CPME should be mainly due to its moderate polarity and high boiling point. Copyright © 2012 John Wiley & Sons, Ltd. 相似文献
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The classical Pinner reaction has been improved by the utilization of 4N-HCl solution in cyclopentyl methyl ether (CPME) as a solvent, wherein direct isolation of the product was possible by a simple filtration. 相似文献
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Hélène PellissierAuthor Vitae 《Tetrahedron》2011,67(21):3769-3802
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The combination of the 5-N-tert-butoxycarbonyl (Boc) group of laurylthio sialoside and cyclopentyl methyl ether (CPME) as a solvent enhanced the reactivity and α-selectivity of the sialyl donor during sialylation. Selective deprotection of the N-Boc group of sialoside, including an acid-sensitive isopropylidene function, was successfully achieved by Yb(OTf)3-SiO2. Transformation of N,N-Ac,Boc into an N-acetylglycolyl group of sialoglycoside was easily performed via selective N-deacylation of the mixed Ac-N-Boc carbamate, subsequent Boc group removal, and acylation. 相似文献
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