Journal
TETRAHEDRON LETTERS
Volume 46, Issue 35, Pages 5803-5806Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2005.06.149
Keywords
biomimetic reactions; cyclization; TiF4; aldehydes; allylsilane
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TiF4 has proven to be the Lewis acid of choice for promoting the biomimetic addition of 2-trimethylsilylmethyl-1,5-dienes to aliphatic aldehydes with concomitant cyclization. 1,3-cis-Disubstituted methylenecyclohexanes are thus produced in good yields and high diastereoselectivity. The reaction appears to proceed via a highly concerted mechanism involving a chair-like transition state. (c) 2005 Elsevier Ltd. All rights reserved.
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