Diastereoselective titanium-mediated construction of cis-2,3-ring annelated 1-(2'-chloroethyl)cyclopropanols |
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| Authors: | Lecornué Frédéric Ollivier Jean |
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| Affiliation: | Laboratoire des Carbocycles, UMR 8615, Institut de Chimie Moléculaire et des Matériaux d'Orsay, Bat. 420, Université de Paris-Sud, 91405 Orsay, France. |
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| Abstract: | Titanium(IV)-mediated cyclopropanation induced by reaction of cycloalkylmagnesium bromides 1a-e in the presence of titanium tetraisopropoxide with ethyl beta-chloropropionate 2 yielded cis-fused 1-(2'-chloroethyl)cyclopropanols 3b-e with diastereoselectivity highly depending on the ring size. Unexpected rearrangement products 5d,e were isolated in some cases. |
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