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Scientific article
English

Boron fluoride promoted opening of epoxides by organocopper or cuprate reagents

Published inTetrahedron, vol. 42, no. 20, p. 5607-5619
Publication date1986
Abstract

In the presence of BF3 the reaction rate of organocopper and cuprate reagents with poorly reactive epoxides is dramatically enhanced. Lithium organocuprates are the best choice among the various organocopper and cuprate reagents tested. Even the dimesityl cyanocuprate is able to react with cyclohexene oxide in excellent yield. No products of cationic rearrangements are observed. The reaction with various epoxides shows a complete stereochemical (pure anti opening) and regiochemical control (attack on the less hindered side of the epoxide).

Affiliation Not a UNIGE publication
Citation (ISO format)
ALEXAKIS, Alexandre, JACHIET, D., NORMANT, Jean F. Boron fluoride promoted opening of epoxides by organocopper or cuprate reagents. In: Tetrahedron, 1986, vol. 42, n° 20, p. 5607–5619. doi: 10.1016/S0040-4020(01)88165-5
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ISSN of the journal0040-4020
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