TY - JOUR
T1 - Synthesis of indenes by ytterbium-catalyzed carboalkoxylation/Friedel- Crafts reaction of arylidenecyclopropanes with acetals
AU - Nakamura, Itaru
AU - Kamada, Michiru
AU - Yamamoto, Yoshinori
PY - 2004/3/29
Y1 - 2004/3/29
N2 - Ytterbium-catalyzed tandem carboalkoxylation/Friedel-Crafts reaction of arylidenecyclopropanes 1 with acetals 2 afforded the corresponding indene derivatives 3 in good to high yields. For example, in the presence of 10mol% of Yb(OTf)3 the reaction of 1-phenylbenzylidenecyclopropane 1a with the dimethyl acetals of benzaldehyde 2a, p-tolualdehyde 2b, and p-anisaldehyde 2c gave 1,3-diphenyl-2-(2-methoxyethyl)indene 3a, 2-(2-methoxyethyl)-3-phenyl-1-(p- tolyl)indene 3b, and 1-(p-anisyl)-2-(2-methoxyethyl)-3-phenylindene 3c in 82%, 80%, and 80% yields, respectively.
AB - Ytterbium-catalyzed tandem carboalkoxylation/Friedel-Crafts reaction of arylidenecyclopropanes 1 with acetals 2 afforded the corresponding indene derivatives 3 in good to high yields. For example, in the presence of 10mol% of Yb(OTf)3 the reaction of 1-phenylbenzylidenecyclopropane 1a with the dimethyl acetals of benzaldehyde 2a, p-tolualdehyde 2b, and p-anisaldehyde 2c gave 1,3-diphenyl-2-(2-methoxyethyl)indene 3a, 2-(2-methoxyethyl)-3-phenyl-1-(p- tolyl)indene 3b, and 1-(p-anisyl)-2-(2-methoxyethyl)-3-phenylindene 3c in 82%, 80%, and 80% yields, respectively.
KW - Carboalkoxylation
KW - exo-Methylenecyclopropane
KW - Friedel-Craft reaction
KW - Indene
KW - Lewis acid catalysis
KW - Ytterbium catalyzed reaction
KW - Ytterbium triflate
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U2 - 10.1016/j.tetlet.2004.02.066
DO - 10.1016/j.tetlet.2004.02.066
M3 - Article
AN - SCOPUS:1642272805
SN - 0040-4039
VL - 45
SP - 2903
EP - 2906
JO - Tetrahedron Letters
JF - Tetrahedron Letters
IS - 14
ER -