Synthesis of 2-substituted bicyclo[1.1.0]butanes zincocyclopropanation using bromoform as the carbenoid precursor

Through a revisited Simmons-Smith type zincocyclopropanation using bromoform as the carbenoid source, the synthesis of 2-, 2,2- and 2,4-substituted bicyclo[1.1.0]butanes is reported. Few antecedents of the derivatives have yet been described. Ultimately, the underexplored scaffolds exhibited a compl...

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Published in:Chemical communications (Cambridge, England) England), 2023-04, Vol.59 (35), p.5273-5276
Main Authors: Thai-Savard, Léa, Charette, André B
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Summary:Through a revisited Simmons-Smith type zincocyclopropanation using bromoform as the carbenoid source, the synthesis of 2-, 2,2- and 2,4-substituted bicyclo[1.1.0]butanes is reported. Few antecedents of the derivatives have yet been described. Ultimately, the underexplored scaffolds exhibited a complete discrepency of reactivity. An efficient 3-step synthesis of bicyclo[1.1.0]butanes from monoprotected 1,2-butenediols is described. The product can be converted to cyclobutanes upon electrophilic activation.
ISSN:1359-7345
1364-548X
DOI:10.1039/d3cc00335c