Abstract
Cyclopropylboronic acid esters 2a-j are prepared conveniently and with high stereoselectivity by cycloaddition of carbenes (or carbenoids) to 1-alkenylboronic acid esters. Methylene transfer is achieved either by the Simmons-Smith reaction or with diazomethane/palladium(II) acetate. The latter procedure is susceptible to steric hindrance, but otherwise, product yields are equally good with both methods. Acyl carbene transfer to vinylboronate 1a succeeds with palladium(II) acetate as catalyst, but not with dirhodium tetraacetate or copper(I) triflate
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