Accessibility navigation


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. ORCID: https://orcid.org/0000-0002-8442-7380, 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

[img]
Preview
Text
· Please see our End User Agreement before downloading.

1MB

It is advisable to refer to the publisher's version if you intend to cite from this work. See Guidance on citing.

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)
Life Sciences > School of Chemistry, Food and Pharmacy > Department of Chemistry
ID Code:58582
Publisher:Royal Society of Chemistry

Downloads

Downloads per month over past year

University Staff: Request a correction | Centaur Editors: Update this record

Page navigation