title: Diastereoselective Simmons-Smith cyclopropanations of allylic amines and carbamates.
abstract: Cyclopropanation of 3-(N,N-dibenzylamino)cyclohexene with either Zn(CH(2)I)(2)(Wittig-Furukawa reagent) or CF(3)CO(2)ZnCH(2)I (Shi's reagent) gives the corresponding syn-cyclopropane as a single diastereoisomer, whilst cyclopropanation of 3-(N-tert-butoxycarbonylamino)cyclohexene with CF(3)CO(2)ZnCH(2)I gives the corresponding anti-cyclopropane exclusively; facile N-deprotection gives access to either diastereoisomer of the trifluoroacetic acid salt of 2-aminobicyclo[4.1.0]heptane.
authors.affiliation: Department of Organic Chemistry, Chemistry Research Laboratory, University of Oxford, Mansfield Road, Oxford, UK OX1 3TA. steve.davies@chem.ox.ac.uk
authors.forename: Stephen G
authors.initials: SG
authors.lastname: Davies
authors.forename: Kenneth B
authors.initials: KB
authors.lastname: Ling
authors.forename: Paul M
authors.initials: PM
authors.lastname: Roberts
authors.forename: Angela J
authors.initials: AJ
authors.lastname: Russell
authors.forename: James E
authors.initials: JE
authors.lastname: Thomson