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Resolution of the chiral iron acetyl complex [(C5H5)Fe(CO)(PPh3)COCH3]

Authors
Journal
Tetrahedron Asymmetry
0957-4166
Publisher
Elsevier
Publication Date
Volume
4
Issue
7
Identifiers
DOI: 10.1016/s0957-4166(00)80348-1

Abstract

Abstract Reaction of the lithium enolate of racemic iron acetyl complex [(C 5H 5)Fe(CO)(PPh 3)COCH 3] with the thiolsulphonate 3, derived from homochiral (1 S-10-mercaptoisoborneol 2, provides the diastercomeric α-sulphides 4 and 5. Selective oxidation of diastereomer 4 to the sulphoxide 6 ( k ox. 4 / k ox. 5 = ca. 20–25) allows facile separation from the sulphide 5. Subsequent desulphurisation of 6 and 5 furnishes the homochiral ( R)-(−)- and ( S)-(+)-acetyl complexes in overall yields (maximum 50%) of 21% and 27% respectively from the racemate.

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