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Chiral biferrocene-based bis(oxazolines): Ligands for Cu(I)-catalyzed asymmetric cyclopropanations of ene-diazoacetates

✍ Scribed by Sung-Gon Kim; Chang-Woo Cho; Kyo Han Ahn

Book ID
104209531
Publisher
Elsevier Science
Year
1999
Tongue
French
Weight
441 KB
Volume
55
Category
Article
ISSN
0040-4020

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✦ Synopsis

Chiral biferrocene-based bis(oxa~aline) compounds, which have both planar and central chirality, are synthesized. The Cu(I)-complexes of the bis(oxa~alinyl)biferracenes were found to be conformationaily flexible and have a wide bite angle (13~') by NMR and molecular modeling studies. The complexes catalyzed the intramolecular cyclopropanation reaction of ene-diazoacetates. and low to moderate enantioselectivities and decreased reactivity were observΒ’~ compared to known malonate-derived bis(oxazoline) systems.

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Synthesis of Chiral Bis(oxazolinyl)biferrocene Ligands and Their Application to Cu(I)-Catalyzed Asymmetric Cyclopropanation. -Five ligands of type (I) are prepared and used as chiral ligands in the Cu-catalyzed asymmetric cyclopropanation of styrene with diazoacetates. Best results concerning the e.