Heterosubstituted cyclopropanation of alkenes with organochromium reagents derived from heterosubstituted dihalomethanes,CrCl2, and tetraalkylethylenediamine |
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Institution: | Division of Chemistry and Biochemistry, Graduate School of Natural Science and Technology, Okayama University, Tsushima, Okayama 700-8530, Japan;Research Center for Materials Science, Nagoya University, Furo-cho, Chikusa-ku, Nagoya, 464-8602 Japan |
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Abstract: | Iodocyclopropanes of trans configuration are produced stereoselectively from terminal alkenes by treatment with a reagent derived from iodoform, chromium(II) chloride, and TEEDA (N,N,N′,N′-tetraethylethylenediamine) in THF. Similarly, cyclopropylsilanes and cyclopropylboronic esters are obtained by using R3SiCHI2, and a combination of Cl2CHB(OR)2 and LiI instead of iodoform, respectively. The heterocyclopropanation occurs selectively at terminal double bonds, and di- and trisubstituted double bonds in the same molecules remain 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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