One-pot allyl-/crotylboration-Prins cyclization of aldehydes |
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Authors: | P. Veeraraghavan Ramachandran Pravin D. Gagare |
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Affiliation: | Herbert C. Brown Center for Borane Research, Department of Chemistry, Purdue University, 560 Oval Drive, West Lafayette, IN 47907-2084, USA |
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Abstract: | Multi-substituted tetrahydropyrans (THPs) have been prepared via a one-pot, In(OTf)3-catalyzed, sequential allyl-/crotylboration-Prins cyclization. The homoallylic borate intermediate formed during the allyl- and crotylboration was converted in situ to an oxocarbenium ion and trapped with a nucleophile. The reaction has been extended to include a one-pot allylboration-cross Prins cyclization as well. |
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Keywords: | Prins cyclization Allylboration Crotylboration Oxocarbenium ion Tetrahydropyran |
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