Diastereoselective Simmons–Smith cyclopropanations of allylic amines and carbamates

Literature Information

Publication Date 2007-08-24
DOI 10.1039/B711358G
Impact Factor 6.222
Authors

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


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Abstract

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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