Diastereoselective Simmons–Smith cyclopropanations of allylic amines and carbamates
Literature Information
Stephen G. Davies, Kenneth B. Ling, Paul M. Roberts, Angela J. Russell, James E. Thomson
Cyclopropanation of 3-(N,N-dibenzylamino)cyclohexene with either Zn(CH2I)2 (Wittig–Furukawa reagent) or CF3CO2ZnCH2I (Shi's reagent) gives the corresponding syn-cyclopropane as a single diastereoisomer, whilst cyclopropanation of 3-(N-tert-butoxycarbonylamino)cyclohexene with CF3CO2ZnCH2I 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.
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