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

被引：13

作者：

BAKER, TM ^{[1
]}

BODWELL, GJ ^{[1
]}

DAVIES, SG ^{[1
]}

EDWARDS, AJ ^{[1
]}

METZLER, MR ^{[1
]}

机构：

[1] DYSON PERRINS LAB,S PARKS RD,OXFORD OX1 3QY,ENGLAND

来源：

TETRAHEDRON | 1993年 / 49卷 / 25期

关键词：

D O I：

10.1016/S0040-4020(01)87273-2

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Treatment of the lithium enolate derived from homochiral (S)-[(eta5-C5H5)Fe(CO)(PPh3)COCH3 5 with benzyne afforded the homochiral phenylacetyl complex (S)-[(eta5-C5H5)Fe(CO)(PPh3)COCH2Ph] 4. Treatment of the lithium enolate derived from 4 with ClCH2OCH2Ph furnished the homochiral alpha-substituted complex (S,S)-(-)-[(eta5-C5H5)-Fe(CO)(PPh3)COCH(CH2OCH2Ph)Ph] 4 (d.e. > 98%), which on decomplexation and debenzylation afforded (S)-(-)-methyl tropinate (S)-2 (e.e. > 98%).

引用

页码：5635 / 5647

页数：13

共 23 条

[11] BASE-DEPENDENT STEREOSELECTIVITY IN REACTIONS OF ACYL LIGAND IN PHENYLACETYLIRON COMPLEX (ETA-5-C5H5)FE(CO)(PPH3)(COCH2PH) [J].