Camphor-based alpha-bromo ketones for the asymmetric Darzens reaction

Authors
Palomo, C Oiarbide, M Sharma, AK Gonzalez-Rego, MC Linden, A Garcia, JM Gonzalez, A
Citation
C. Palomo et al., Camphor-based alpha-bromo ketones for the asymmetric Darzens reaction, J ORG CHEM, 65(26), 2000, pp. 9007-9012
Citations number
46
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
JOURNAL OF ORGANIC CHEMISTRY
ISSN journal
00223263 → ACNP
Volume
65
Issue
26
Year of publication
2000
Pages
9007 - 9012
Database
ISI
SICI code
0022-3263(200012)65:26<9007:CAKFTA>2.0.ZU;2-U
Abstract
(1R)-2-endo-Bromoacetyl-1,7, 7-trimethylbicyclo [2.2.1]heptan-2-ol (endo-2- bromoacetylisoborneol) 4 and its trimethylsilyl ether 3 are presented as ef ficient reagents for the asymmetric Darzens reaction. From the alpha,beta - epoxy ketone adducts the chiral inductor camphor is removed, by treatment w ith ceric(IV) ammonium nitrate, to yield the corresponding epoxy acids whic h are isolated as their dicyclohexylammonium salts.