4.4 Article

Direct synthesis of tetrahydropyrans via one-pot Babier-Prins cyclization of allylbromide with carbonyl compounds promoted by RTILs BPyX/SnX′2 or BBIMBr/SnBr2

Journal

TETRAHEDRON
Volume 62, Issue 29, Pages 7113-7120

Publisher

PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2006.04.075

Keywords

Babier-Prins cyclization; allylbromide; carbonyl compound; BBIMBr/SnBr2; tetrahydropyran; direct synthesis

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Tetrahydropyran compounds can be directly synthesized from allylbromide and carbonyl compounds by means of one-pot Babier-Prins cyclization promoted by BPyX/SnX'(2) or BBINBr/SnBr2 complex (functionalized RTILs) under solvent-free conditions. 2,6-Homo-bissubstituted- and 2,6,6-trisubstituted, especially 6-(spirocycloalkyl)-, tetralrydropyran compounds can be prepared in good yields. (c) 2006 Elsevier Ltd. All rights reserved.

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