A General Solid-Phase Synthesis Strategy for the Preparation of 2-Pyrrolidinemethanol Ligands

Journal of Organic Chemistry

Volumn 60, Issue 24, 1995, Pages 7712-7713

  Liu, Guangcheng ^a   Ellman, Jonathan A ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 10244273514     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo00129a002     Document Type: Article

References (13)

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5. Soai, K.; Ookawa, A.; Kaba, T.; Ogawa, K. J. Am. Chem. Soc. 1987, 109, 7111.
6. Good enantioselectivities are observed for aliphatic substrates with other Iigand classes: Yakahashi, H.; Kawakita, T.; Yoshioka, M.; Kobayashi, S.; Ohno, M. Tetrahedron Lett. 1989, 30, 7095.
7. Schmidt, B.; Seebach, D. A. Angew. Chem., Int. Ed. Engl. 1991, 30, 99.
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9. Kanth, J. V. B.; Periasamy, M. Tetrahedron 1993, 49, 5127.
10. An amine protecting group is necessary, since many researchers have reported that Grignard additions to proline methyl ester results in extensive racemization when the free amine is employed, Mathre, D. J.; Jones, T. K.; Xavier, L. C.; Blacklock, T. J.; Reamer, R. A.; Mohan, J. J.; Jones, E. T. T.; Hoogsteen, K.; Baum, M. W.; Grabowski, E. J. J. J. Org. Chem. 1991, 56, 751.
11. Ookawa, A.; Soai, K. J. Chem. Soc, Perkin Trans. 1 1987, 1465.
12. Corey, E. J.; Bakshi, R. K.; Shibata, S.; Chen, C.; Singh, V. K. J. Am. Chem. Soc 1987, 109, 7925.
13. For a recent review of ligand-accelerated catalysis, see: Berr-isfbrd, D. J.; Bolm, C.; Sharpless, K. B. Angew. Chem., Int. Ed. Engl. 1995, 34, 1059.