Copper-mediated SN2’ Allyl-Alkyl and Allyl-Boryl Couplings of Vi- nyl Cyclic Carbonates

Author

Miralles, Núria

Gómez, José Enrique

Kleij, Arjan W.

Fernández, Elena

Publication date

2017-10-27



Abstract

A method for the copper-catalyzed borylmethylation and borylation of vinyl cyclic carbonates through an SN2’ mech- anism is reported. These singular reactions involve selective SN2’ allylic substitutions with concomitant ring opening of the cyclic carbonate, and with extrusion of CO2 and formation of a useful hydroxyl functionality in a single step. The stereoselectivity of the homoallylic borylation and allylic borylation processes can be controlled, and synthetically useful unsaturated (E)-pent-2-ene-1,5- diols and (E)-but-2-ene-1,4-diols accessed.

Document Type

Article
Accepted version

Language

English

Subject

54

Pages

6096 p.

Documents

Org. Lett. 2017, 19, 6096-6099 (KLEIJ).pdf

1.009Mb

 

Rights

L'accés als continguts d'aquest document queda condicionat a l'acceptació de les condicions d'ús establertes per la següent llicència Creative Commons:http://creativecommons.org/licenses/by-nc-nd/4.0/

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