Enantioselective synthesis of planar chiral ortho-functionalized ferrocenyl ketones

Authors
Enders, D Peters, R Lochtman, R Runsink, J
Citation
D. Enders et al., Enantioselective synthesis of planar chiral ortho-functionalized ferrocenyl ketones, EUR J ORG C, (16), 2000, pp. 2839-2850
Citations number
25
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
ISSN journal
1434193X → ACNP
Issue
16
Year of publication
2000
Pages
2839 - 2850
Database
ISI
SICI code
1434-193X(200008):16<2839:ESOPCO>2.0.ZU;2-U
Abstract
An efficient and flexible asymmetric synthesis of planar chiral ortho-funct ionalized ferrocenyl ketones in good overall yields (35-79%) and enantiomer ic excesses (ee = 71-96%) is described. The key step of the procedure is th e diastereoselective (de = 87-98%) orthometalation of ferrocenyl ketone SAM P hydrazones, followed by trapping with various electrophiles such as Mel, Me3SiCl, Ph2PCl, Ph2CO, Me2NCHO or I-2. Subsequent oxidative or reductive h ydrazone cleavage leads to the title compounds.