Davies铁手性助剂

Davies铁手性助剂,酰基羰基(eta5-2,4-环戊二烯-1-基)(三苯基膦)铁。可以用于不对称的Michael加成反应,不对称的aldol反应、不对称合成α或β取代的羧酸和不对称合成β内酯或β内酰胺等反应。此手性试剂可以用溴氧除去。

【Davies SG, Synlett 1991779】

反应实例

(RR/SS)-[(h5-C5H5)Fe(CO)(PPh4)COCH2CH(Me)NHCH2Ph] (3). n-BuLi (0.4 mL, 0.64 mmol) was added to PhCH2NH2 (70 mg, 0.66 mmol) in THF (20 mL) at -20 C to give a purple solution. After 1 h stirring at 20 C, this was added to 13,4 (250 mg, 0.52 mmol) in THF (30 mL) at -78 C. MeOH (66.5 mg, 2.08 mmol) was added and the mixture was stirred for 1 h at -78 C. After evaporation of solvent, the residue was dissolved in DCM, filtered (Celite) and

chromatographed (alumina, DCM:EA:MeOH 10:9:1) to afford 690 mg (90%) of 3, as a single diastereoisomer,

(4S)-(-)4-Methyl-N-benzyl-b-lactam (4). Oxidation of 3 with Br2 in DCM at -40 C followed by chromatography on silica gel (Merck 60 H, hexane:Et2O 2:1) gave some of the iron complex, while elution with the same solvents 1:2 afforded 106 mg of 3 (65%)

【Davies SG, Tetrahedron, 1986, 42, 5123】

相关文献

1 Davies SG Chem Comm 1982 1303

2 Davies SG Chem Comm 1985 607

3 Davies SG J Organomet Chem 1985 296 C40

4 Davies SG Tetrahedron 1986 42 175

5 Davies SG Tetrahedron 1986 42 5123

6 Davies SG Aldrichimica Acta 1990 23 31

7 Davies SG J Chem Soc Chem Comm 2004 2778

8 Davies SG J Organomet Chem 2004 689 4184

编译自:Organic Syntheses Based On Name Reactions, 3RdEd, A. Hassner, Page117.

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