TY - JOUR
T1 - Stereoselective Iodocyclopropanation of Terminal Alkenes with Iodoform, Chromium(II) Chloride, and N,N,N′,N′-Tetraethylethylenediamine
AU - Takai, Kazuhiko
AU - Toshikawa, Shota
AU - Inoue, Atsushi
AU - Kokumai, Ryo
PY - 2003/10/29
Y1 - 2003/10/29
N2 - Chemoselectivity of a reagent for (E)-olefination of aldehydes derived by reduction of iodoform with chromium(II) chloride in THF changes markedly by addition of TEEDA (N,N,N-,N-tetraethylethylenediamine), and trans-iodocyclopropanes are produced stereoselectively from terminal alkenes by treatment with the base-added reagent system. The iodocyclopropanation occurs only at terminal double bonds, and di- and trisubstituted double bonds in the same molecules remained unchanged. Such functional groups as alcohol, ether, silyl ether, ester, tertiary amine, and amide groups are compatible with the reaction conditions.
AB - Chemoselectivity of a reagent for (E)-olefination of aldehydes derived by reduction of iodoform with chromium(II) chloride in THF changes markedly by addition of TEEDA (N,N,N-,N-tetraethylethylenediamine), and trans-iodocyclopropanes are produced stereoselectively from terminal alkenes by treatment with the base-added reagent system. The iodocyclopropanation occurs only at terminal double bonds, and di- and trisubstituted double bonds in the same molecules remained unchanged. Such functional groups as alcohol, ether, silyl ether, ester, tertiary amine, and amide groups are compatible with the reaction conditions.
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U2 - 10.1021/ja0373061
DO - 10.1021/ja0373061
M3 - Article
C2 - 14570448
AN - SCOPUS:0142245600
SN - 0002-7863
VL - 125
SP - 12990
EP - 12991
JO - Journal of the American Chemical Society
JF - Journal of the American Chemical Society
IS - 43
ER -