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. AnastasiaPrimo
;E. GianniniSecondo
;
2005
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.
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