Beilstein J. Org. Chem.2008,4, No. 38, doi:10.3762/bjoc.4.38
some degree of isomerisation to (aminomethyl)indenes 22 and 25 respectively were observed, as indicated by the appearance of vinylic CH resonances in the 1H NMR spectra (δ 6.8–6.0). This isomerisation is presumably the result of trace acidcatalysis, with the process likely proceeding via protonation
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Graphical Abstract
Scheme 1:
Cyclopropylmethyl–homoallyl and nortricyclyl–norbornenyl radical systems.
Beilstein J. Org. Chem.2007,3, No. 16, doi:10.1186/1860-5397-3-16
under Lewis acidcatalysis. [10] Thus, silicon assisted cyclization of oxoallylsilanes 3–8 in the presence of TiCl4 or EtAlCl2 results in the formation of 3-methylene-1-cyclopentanols 11–14 with a high degree of stereocontrol (Scheme 3). [7] The cis stereochemistry observed in 11 might indicate a