Diastereoselective titanium-mediated construction of cis-2,3-ring annelated 1-(2'-chloroethyl)cyclopropanols.
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.
Lecornué
Frédéric
F
Laboratoire des Carbocycles, UMR 8615, Institut de Chimie Moléculaire et des Matériaux d'Orsay, Bât. 420, Université de Paris-Sud, 91405 Orsay, France.
Ollivier
Jean
J