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.

TiF4-mediated biomimetic alkylation–cyclization cascade reaction of 2-trimethylsilylmethyl-1,5-dienes with aldehydes / L. Anastasia, E. Giannini, G. Zanoni, G. Vidari. - In: TETRAHEDRON LETTERS. - ISSN 0040-4039. - 46:35(2005 Aug 29), pp. 5803-5806.

TiF4-mediated biomimetic alkylation–cyclization cascade reaction of 2-trimethylsilylmethyl-1,5-dienes with aldehydes

L. Anastasia
Primo
;
E. Giannini
Secondo
;
2005-08-29

Abstract

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.
Settore BIO/10 - Biochimica
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/2434/27807
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