Journal
TETRAHEDRON LETTERS
Volume 50, Issue 12, Pages 1298-1300Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2009.01.012
Keywords
Tetrahydrofuran; Neighboring group participation; Iodosylbenzene; Hypervalent iodine; Chiral auxiliary
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Funding
- Japan Society for the Promotion of Science (JSPS) [19550050]
- Grants-in-Aid for Scientific Research [19550050] Funding Source: KAKEN
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Reaction of but-3-enyl camphanate and its derivatives with iodosylbenzene yielded tetrahydrofuran-3-yl camphanate with high diastereomeric ratio via a 1,3-dioxan-2-yl cation intermediate. The reaction using (IS)-camphanate as a chiral auxiliary preferentially gave (S)-3-acyloxytetrahydrofuran and (2S,3S)-3-acyloxy-2-silyltetrahydrofuran. (C) 2009 Elsevier Ltd. All rights reserved.
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