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Asymmetric synthesis of 2,4-disubstituted butyrolactones using the iron chiral auxiliary [(η5-C5H5)Fe(CO)(PPh3)]

Authors
Journal
Tetrahedron
0040-4020
Publisher
Elsevier
Publication Date
Volume
46
Identifiers
DOI: 10.1016/s0040-4020(01)85598-8

Abstract

Abstract Treatment of the lithium enolate derived from homochiral S-[(n 5η-C 5H 5)Fe(CO)(PPh 3)COCH 2CH 3] with homochiral R- or S-propylene oxide or R-styrene oxide in the presence of diethylaluminium chloride followed by oxidative decomplexation generated cis-2S,4R-dimethyl butyrolactone, trans-2S,4S-dimethyl butyrolactone and cis-2S,4S-2-methyl-4-phenyl butyrolactone respectively. An X-ray crystal structure of the latter compound established unambiguously the relative and absolute configurations. Treatment of the lithium enolate from homochiral R-[(ηn 5-C 5H 5)Fe(CO)(PPh 3)COCH 2CH 3]with R-styrene oxide in the presence of diethylaluminium chloride followed by oxidative decomplexation generated trans-2R,4S-2-methyl-4-phenyl butyrolactone. In the presence of diethylaluminium chloride the enolate from S-[(η 5-C 5H 5)Fe(CO)(PPh 3)COCH 2CH 3] with racemic styrene oxide exhibited chiral discrimination in favour of the R-epoxide to the extent of 100:1

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