Kinetic Resolution of Racemic Ferrocenylphosphine Compounds by Enantioselective Oxidation Using Cyclic Selenoxides Having a Chiral Ligand

Cyclic selenoxides having an optically active binaphthyl skeleton work as the reagents for enantioselective oxidation of phosphines to the corresponding phosphine oxides. Treatment of a racemic 2-oxazolin-2-ylferrocenylphosphine with one of the selenoxides in carbon tetrachloride in the presence of...

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Published inBulletin of the Chemical Society of Japan Vol. 76; no. 2; pp. 381 - 387
Main Authors Miyake, Yoshihiro, Yamauchi, Akiyoshi, Nishibayashi, Yoshiaki, Uemura, Sakae
Format Journal Article
LanguageEnglish
Published TOKYO The Chemical Society of Japan 01.02.2003
Chemical Soc Japan
Chemical Society of Japan
Subjects
Chemistry
Chemistry, Multidisciplinary
Physical Sciences
Science & Technology
ORTHO-LITHIATION
ASYMMETRIC-SYNTHESIS
SUBSTITUTED FERROCENES
DIPHOSPHINES
REDUCTION
PLANAR CHIRALITY
SELENIDES
PHOSPHINE OXIDES
SALTS
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Summary:Cyclic selenoxides having an optically active binaphthyl skeleton work as the reagents for enantioselective oxidation of phosphines to the corresponding phosphine oxides. Treatment of a racemic 2-oxazolin-2-ylferrocenylphosphine with one of the selenoxides in carbon tetrachloride in the presence of phenol affords the corresponding phosphine oxide together with the unreacted starting phosphine, both with moderate enantioselectivities (the phosphine oxide, up to 13% ee; the phosphine, up to 29% ee).
ISSN:0009-2673
1348-0634
DOI:10.1246/bcsj.76.381