Journal
TETRAHEDRON LETTERS
Volume 46, Issue 39, Pages 6679-6682Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2005.07.142
Keywords
chromium; catalysis; cyclization; pinacols; silylation
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The choice of the sityl scavenger shows a substantial influence on the diastereoselectivity of the chromium catalyzed pinacol cross coupling. In the case of the intramolecular cyclization, two competing effects are observed. If the silylation reagents contain chelating heteroatoms in the side chain, a remarkable trans-selectivity is observed. Conversely the cis-diols are preferred if bulky substituted scavengers are used. A suitable transition state model for this reaction is reported, based on formerly published results. (c) 2005 Elsevier Ltd. All rights reserved.
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