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DOI: 10.1055/sos-SD-036-00360

Scott, P. J. H.; Steel, P. G.Science of Synthesis, (200836467.

A means of generating alkoxycarbenes under mild conditions that avoids either the need for potentially carcinogenic chloromethyl ethers or the necessity for the multistep preparation of Fischer carbenoid complexes is realized in reactions between orthoformates and alkenes that are promoted by a combination of zinc(II) chloride and chlorotrimethylsilane. The process leads to the formation of cyclopropyl ethers, such as methyl 2-methyl-2-phenylcyclopropyl ether (3) from isopropenylbenzene (2) (Scheme 1), in moderate yields and diastereoselectivity. However, despite the simplicity of the process and the availability of suitable ortho esters, deprotection of the product ethers to give the corresponding cyclopropanols remains to be demonstrated.[‌68‌]

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