The Synthesis of Aracemic 4-Substituted Pyrrolidinones and 3-Substituted Pyrrolidines. An Asymmetric Synthesis of (−)-Rolipram

Journal of Organic Chemistry

Volumn 58, Issue 1, 1993, Pages 36-42

  Meyers, A I ^a   Snyder, Lawrence ^a  

^a Veterinary Dentistry and Oral Surgery   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

PYRROLIDINE DERIVATIVE; ROLIPRAM;

ARTICLE; REACTION ANALYSIS; SYNTHESIS;

EID: 0027535582     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo00053a012     Document Type: Article

References (23)

1. Meyers, A. I.; Snyder, L. J. Org. Chem. 1992, 57, 3814.
2. Romo, D.; Meyers, A. I. Tetrahedron Rep. 1991, 47, 9603.
3. 4 gave the stated yields on smaller scale (<100 mg), but when scale-up was attempted subsequent to the publication, the yields were erratic and generally low (26–36%) (B. Newhouse, research in progress).
4. Meyers, A. I.; Fray, A. H. Tetrahedron Lett. 1992, 33, 3675.
5. Busacca, C. A.; Meyers, A. I. J. Chem. Soc., Perkin Trans. 1 1991, 2299.
6. Meyers, A. I.; Burgess, L. E. Unpublished results.
7. Ram, S.; Ehrenkaufer, R. E. Synthesis 1988, 91.
8. 4 see Mukaiyama, T. Angew. Chem., Int. Ed. Engl. 1977, 16, 817.
9. Burgess, L. E.; Meyers, A. I. J. Am. Chem. Soc. 1991, 113, 9868.
10. Zelle, R. E. Synthesis 1991, 1023.
11. Meyers, A. I.; Burgess, L. E. J. Org. Chem. 1991, 56, 2294.
12. Saito, S.; Nakajima, H.; Inaba, M.; Moriwake, T. Tetrahedron Lett. 1989, 30, 837.
13. Schmiechen, R.; Horowski, R.; Palenschat, D.; Paschelke, G.; Wachtel, H.; Kehr, W. U.S. Patent 4 193 926, 1980.
14. Clive, D. L. J.; Angoh, A. G.; Bennett, S. M. J. Org. Chem. 1987, 52, 1339.
15. Green, K. J. Org. Chem. 1992, 56, 4325.
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17. After this manuscript was submitted for publication, a beautiful asymmetric route to Rolipram was reported: Mulzer, J.; Zuhse, R.; Schmiechen, R. Angew. Chem., Int. Ed. Engl. 1992, 31, 870.
18. For other methods to prepare 3-substituted pyrrolidines, see: Roussi, G.; Zhang, J. Tetrahedron 1991, 47, 5161.
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23. B Receptors in Mammalian Function, J. tWiley & Sons: New York, 1990.