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 / Anastasia, L.; Giannini, E.; Zanoni, G.; Vidari, G.. - In: TETRAHEDRON LETTERS. - ISSN 0040-4039. - 46:35(2005), pp. 5803-5806. [10.1016/j.tetlet.2005.06.149]
TiF4-mediated biomimetic alkylation–cyclization cascade reaction of 2-trimethylsilylmethyl-1,5-dienes with aldehydes
L. Anastasia;
2005-01-01
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.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
