Chiral Mn-salen catalyzed enantiotopic selective C-H oxidation of meso- pyrrolidine derivatives

Tetrahedron Letters

Volumn 39, Issue 45, 1998, Pages 8295-8298

  Punniyamurthy, T ^a   Miyafuji, Akio ^a   Katsuki, Tsutomu ^a  

^a KYUSHU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

HETEROCYCLIC COMPOUND; PYRROLIDINE DERIVATIVE;

ARTICLE; CATALYSIS; CHIRALITY; ENANTIOMER; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; OXIDATION;

EID: 0032487794     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)80001-4     Document Type: Article

References (19)

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12. i) Kawasaki, K.; Katsuki, T. Tetrahedron 1997, 53, 6337-6350.
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15. 4. Bettoni, G.; Cellucci, C.; Beradi, F. J. Hetereocyclic Chem. 1980, 17, 603.
16. 5. 2-Hydroxypyrrolidines (3a, 5a and 6a) could not be separated from the corresponding starting materials (2a, 5 and 6) and they were isolated as lactams (4a, 5b and 6b) alter Jones oxidation. Unreacted starting material was recovered intact, except for the examples described in Table 2 (entries 7-10).
17. 6. Pentafluoroiodosylbenzene (44.3mg, 0.14 mmol) was added in one portion to a precooled solution of N-phenylacetylated 3,4-dimelhyl pyrrolidine 5 (31 mg, 0.14 mmol) and 1b (2.2mg, 2 mol%) in acetonitrile (2 ml) under nitrogen at -25 °C. After stirring 17 h, the reaction mixture was quenched by adding dimethyl sulfide and concentrated in vacuo. The residue was passed through a short column of silica gel (ethyl acetate/hexane= 2:3) to afford hydroxypyrrolidine derivative 5a which was further oxidized to lactam 5b by Jones reagent. After purification by silica gel column chromatography using ethyl acetate/hexane (1:4), the optical purity was determined to be 84% ee by HPLC using optically active column (DAICEL CHIRALPAK AD, hexane/isopropanol= 100:1).
18. 7. Malsuki, K.; Inoue, H.; Ishida, A.; Takeda, M.: Nakagawa, M.; Hino, T. Chem. Pharm. Bull. 1994, 42(1), 9-18.
19. 8. Although the configurations of compounds 5b and 6b are unknown, they showed the same positive specific rotation as compound 4. Therefore, configurations of 5b and 6b were tentatively assigned as described in Scheme 1.