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Synfacts 2008(12): 1319-1319
DOI: 10.1055/s-0028-1083593
DOI: 10.1055/s-0028-1083593
Metal-Mediated Synthesis
© Georg Thieme Verlag
Stuttgart ˙ New York
Tandem Cyclopropanation with CH2Br2 under Grignard Conditions
G. Brunner, L. Eberhard, J. Oetiker, F. Schröder*
Givaudan Schweiz AG, Dübendorf, Switzerland
Further Information
Publication History
Publication Date:
20 November 2008 (online)

Significance
An efficient cyclopropanation of allylic Mg and Li alcoholates using dibromomethane is described. Reaction rates depend on the substitution pattern of the alcoholates, with α-substituted substrates giving excellent syn selectivity. Furthermore, conjugated aldehydes, ketones and esters have been alkylated using magnesium or lithium reagents yielding intermediate allylic alcoholates which were subsequently cyclopropanated using CH2Br2.