The combination of anionic and radical reactions to oxidative tandem processes exemplified by the synthesis of functionalized pyrrolidines [2]

Journal of the American Chemical Society

Volumn 122, Issue 21, 2000, Pages 5212-5213

  Jahn, Ullrich ^a   Müller, Markus ^a   Aussieker, Susanne ^a  

^a TECHNICAL UNIVERSITY OF BRAUNSCHWEIG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

AMIDE; ANION; LITHIUM; PYRROLIDINE DERIVATIVE; RADICAL;

CHEMICAL REACTION; CYCLIZATION; LETTER; OXIDATION; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 0343237801     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja000565v     Document Type: Letter

References (17)

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2. (b) Chem. Rev. 1996, 96, 6, issue 1.
3. Review on electron transfer-induced reactions: Dalko, P. I. Tetrahedron 1995, 51, 7579.
4. Review: Molander, G. A.; Harris, C. R. Tetrahedron 1998, 54, 3321.
5. (a) Cohen, T.; McNamara, K.; Kuzemko, M. A.; Ramig, K.; Landi, J. J., Jr.; Dong, Y. Tetrahedron 1993, 49, 7931.
6. 3, see:
7. Melikyan, G. G. Org. React. 1997, 49, 427.
8. For amide conjugate additions, see: (a) Juaristi, E. Enantioselective Synthesis of β-Amino Acids; Wiley-VCH: Weinheim, 1997. For more recent results, see:
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10. For the use of 5,6, see: (a) Jahn, U.; Hartmann, P. Chem. Commun. 1998, 209.
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12. Although the overall yields are only in the 50% range for 1b, the average yield of each sequence step from 2 is at least 88%.
13. Similar results were reported in related investigations: Asao, N.; Uyehara, T.; Yamamoto, Y. Tetrahedron 1990, 46, 4563.
14. For a review on chelation in radical reactions, see: Renaud, P.; Gerster, M. Angew. Chem., Int. Ed. 1998, 37, 2562.
15. a) Beckwith, A. L. J.; Schiesser, C. H. Tetrahedron 1985, 41, 3925.
16. (b) Spellmeyer, D. C.; Houk, K. N. J. Org. Chem. 1987, 52, 959.
17. Lung-min, W.; Fischer, H. Helv. Chim. Acta 1983, 66, 138.