Diastereoselective Simmons-Smith cyclopropanations of allylic amines and carbamates

Stephen G Davies; Kenneth B Ling; Paul M Roberts; Angela J Russell; James E Thomson

doi:10.1039/b711358g

Diastereoselective Simmons-Smith cyclopropanations of allylic amines and carbamates

Chem Commun (Camb). 2007 Oct 21:(39):4029-31. doi: 10.1039/b711358g. Epub 2007 Aug 24.

Authors

Stephen G Davies¹, Kenneth B Ling, Paul M Roberts, Angela J Russell, James E Thomson

Affiliation

¹ Department of Organic Chemistry, Chemistry Research Laboratory, University of Oxford, Mansfield Road, Oxford, UK OX1 3TA. steve.davies@chem.ox.ac.uk

PMID: 17912405
DOI: 10.1039/b711358g

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.