Abstract
Various new 2-alkenyl-substituted methyl 2-(tert-butyldimethylsiloxy)cyclopropanecarboxylates 8-14 were synthesized from siloxy dienes and methyl diazoacetate. Further substitution by deprotonation and reactions with electrophiles provided derivatives 15-19 in good yields. Reduction of trans-configurated cyclopropanecarboxylates with LiAlH4 afforded the corresponding trans-2-(tert-butyldimethylsiloxy)-1-(hydroxymethyl)cyclopropanes in excellent yields. The related cis-compounds were not formed, but ring-opened products derived thereof were isolated. This unexpected influence of the configuration of the starting material on the type of the product formed is discussed.
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