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26.3.2.1.3.1 Variation 1: Cyclopropanation of Silylketene Acetals

DOI: 10.1055/sos-SD-026-00451

Salaün, J.Science of Synthesis, (200526615.

Cyclopropanation of silylketene acetals 47 by the use of diethylzinc and diiodomethane provides the cyclopropanone acetals 48 (R4=H) in high yield, which can be isolated by distillation after a nonaqueous workup. Use of 1,1-diiodoethane and (diiodomethyl)benzene in combination with diethylzinc leads to methyl- and phenyl-substituted cyclopropan­ones 48 (R4=Me, Ph) respectively, also in high yields. Subsequent chemoselective meth­anolysis provides the cyclopropanone hemiacetals 49 quantitatively (Scheme 19).[‌70‌]

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