Stereoselective reduction of benzils: A new convenient route to enantiomerically pure 1,2-diarylethanediols

Journal of Organic Chemistry

Volumn 61, Issue 11, 1996, Pages 3888-3889

  Prasad, K R K ^a   Joshi, N N ^a  

^a NATIONAL CHEMICAL LABORATORY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000812982     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo952017j     Document Type: Article

References (13)

1. Whitesell, J. K. Chem. Rev. 1989, 89, 1581.
2. Wang, Z.-M.; Sharpless, K. B. J. Org. Chem. 1994, 59, 8302 and references cited therein.
3. Singh, V. K. Synthesis 1992, 605.
4. Maier, G.; Roth, C.; Schmitt, R. K. Chem. Ber. 1985, 118, 704 and references cited therein.
5. Surprisingly, aliphatic 1,2-diones yielded erythro diols exclusively.
6. (a) Quallich, G. J.; Woodall, T. M. Synlett 1993, 929.
7. (b) Corey, E. J.; Bakshi, R. K.; Shibata, S. J. Am. Chem. Soc. 1987, 109, 5551.
8. (a) Muller-Westerhoff, U. T.; Ming Zhou J. Org. Chem. 1994, 59, 4988.
9. (b) Corey, E. J.; Lee, D.-H.; Sarshar, S. Tetrahedron Assym. 1995, 6, 3 and references cited therein.
10. While the manuscript for this paper was under preparation, the use of the catalyst 1b for the reduction of benzil was reported to be 4% de (52:48 for threo:erythro): Quallich, G. J.; Keavey, K. N.; Woodall, T. M. Tetrahedron Lett. 1995, 36, 4729. This variation of diastereoselectivity can be attributed to the difference in the reaction conditions as compared to those in the present study.
11. Berti, G.; Bottari, F. J. Org. Chem. 1960, 25, 1286.
12. Armarego, W. L. F.; Perrin, D. D. Purification of Laboratory Chemicals; Pergamon Press: New York, 1988.
13. Kanth, J. V. B.; Periasamy, M. Tetrahedron 1993, 49, 5127.