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Issue 39, 2007
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Diastereoselective Simmons–Smith cyclopropanations of allylic amines and carbamates

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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.

Graphical abstract: Diastereoselective Simmons–Smith cyclopropanations of allylic amines and carbamates

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Publication details

The article was received on 25 Jul 2007, accepted on 14 Aug 2007 and first published on 24 Aug 2007


Article type: Communication
DOI: 10.1039/B711358G
Citation: Chem. Commun., 2007,0, 4029-4031
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    Diastereoselective Simmons–Smith cyclopropanations of allylic amines and carbamates

    S. G. Davies, K. B. Ling, P. M. Roberts, A. J. Russell and J. E. Thomson, Chem. Commun., 2007, 0, 4029
    DOI: 10.1039/B711358G

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