4.4 Article

Highly stereocontrolled synthesis of fluorinated 2,6-trans dihydropyrans via Prins cyclization

Journal

TETRAHEDRON LETTERS
Volume 51, Issue 7, Pages 1041-1043

Publisher

PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2009.12.068

Keywords

Fluorine chemistry; trans-Dihydropyrans; Prins cyclization; Allenic alcohols; BF3 center dot Et2O

Funding

  1. Singapore Ministry of Education Academic Research [T206B1221, T207B1220RS]

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A highly efficient method for the synthesis of fluorinated 2,6-trans dihydropyrans via BF3 center dot Et2O-promoted Prins cyclization of allenic alcohols and aldehydes is developed. Various 2,6-trans fluorodihydropyrans are obtained in moderate to good yields with excellent diastereoselectivities. (C) 2010 Elsevier Ltd. All rights reserved.

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