ASYMMETRIC-SYNTHESIS OF (S)-(-)-METHYL TROPINATE - APPLICATION OF THEIRON ACYL COMPLEX (S)-(-[(ETA-5-C5H5)FE(CO)(PPH3)COCH2PH] AS A HOMOCHIRAL PHENYLACETATE ENOLATE EQUIVALENT())

Authors
BAKER TM BODWELL GJ DAVIES SG EDWARDS AJ METZLER MR
Citation
Tm. Baker et al., ASYMMETRIC-SYNTHESIS OF (S)-(-)-METHYL TROPINATE - APPLICATION OF THEIRON ACYL COMPLEX (S)-(-[(ETA-5-C5H5)FE(CO)(PPH3)COCH2PH] AS A HOMOCHIRAL PHENYLACETATE ENOLATE EQUIVALENT()), Tetrahedron, 49(25), 1993, pp. 5635-5647
Citations number
23
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
49
Issue
25
Year of publication
1993
Pages
5635 - 5647
Database
ISI
SICI code
0040-4020(1993)49:25<5635:AO(T-A>2.0.ZU;2-L
Abstract
Treatment of the lithium enolate derived from homochiral (S)-[(eta5-C5 H5)Fe(CO)(PPh3)COCH3 5 with benzyne afforded the homochiral phenylacet yl complex (S)-[(eta5-C5H5)Fe(CO)(PPh3)COCH2Ph] 4. Treatment of the li thium enolate derived from 4 with ClCH2OCH2Ph furnished the homochiral alpha-substituted complex S)-(-)-[(eta5-C5H5)-Fe(CO)(PPh3)COCH(CH2OCH 2Ph)Ph] 4 (d.e. > 98%), which on decomplexation and debenzylation affo rded (S)-(-)-methyl tropinate (S)-2 (e.e. > 98%).