What is it about?
Cyclopropanols are versatile intermediates in organic synthesis, but efficient methods for preparing them remain limited. In this work, we developed a new approach that combines ketone-derived lithium enolates with magnesium carbenoids. By exploiting the electrophilic reactivity of magnesium carbenoids, the two components form two carbon–carbon bonds in sequence, providing cyclopropanols in a convenient one-pot process.
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Why is it important?
Our strategy constructs the cyclopropanol ring directly from two readily prepared reaction partners—a ketone and a magnesium carbenoid. This work also highlights a valuable aspect of magnesium carbenoid chemistry: their electrophilic reactivity toward carbon nucleophiles.
Perspectives
This study demonstrates that the electrophilic nature of magnesium carbenoids can be harnessed for carbon–carbon bond formation with enolates. The concept of assembling strained-ring molecules from simple carbonyl compounds and carbenoids may provide a platform for developing new reactions and expanding the synthetic applications of magnesium carbenoids.
Associate Professor Tsutomu Kimura
Read the Original
This page is a summary of: A novel one-pot synthesis of cyclopropanols based on the reaction of magnesium carbenoids with lithium enolate of ketones, Tetrahedron Letters, May 2013, Elsevier,
DOI: 10.1016/j.tetlet.2013.03.025.
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