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Chemoselective and stereoselective lithium carbenoid mediated cyclopropanation of acyclic allylic alcohols

Durán-Peña, M. J., Flores-Giubi, M. E., Botubol-Ares, J. M., Harwood, L. M., Collado, I. G., Macías-Sánchez, A. J. and Hernández-Galán, R. (2016) Chemoselective and stereoselective lithium carbenoid mediated cyclopropanation of acyclic allylic alcohols. Organic and Biomolecular Chemistry, 14 (9). pp. 2731-2741. ISSN 1477-0520

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To link to this item DOI: 10.1039/C5OB02617B

Abstract/Summary

The reaction of geraniol with different lithium carbenoids generated from n-BuLi and the corresponding dihaloalkane has been evaluated. The reaction occurs in a chemo and stereoselective manner, which is consistent with a directing effect from the oxygen of the allylic moiety. Furthermore, a set of polyenes containing allylic hydroxyl or ether groups were chemoselectively and stereoselectively converted into the corresponding gemdimethylcyclopropanes in one single step in moderate to good yields mediated by a lithium carbenoid generated in situ by reaction of n-BuLi and 2,2-dibromopropane.

Item Type:Article
Refereed:Yes
Divisions:Interdisciplinary centres and themes > Chemical Analysis Facility (CAF)
Faculty of Life Sciences > School of Chemistry, Food and Pharmacy > Department of Chemistry
ID Code:58582
Publisher:Royal Society of Chemistry

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