High 1,6 diastereoselectivity in the hydride reduction of an acyclic ketone substrate via bicyclic chelation control

Tetrahedron Letters

Volumn 37, Issue 44, 1996, Pages 7897-7900

  Zhang, Han Cheng ^a   Harris, Bruce D ^a   Maryanoff, Cynthia A ^a   Maryanoff, Bruce E ^a  

^a JOHNSON AND JOHNSON PHARMACEUTICAL RESEARCH AND DEVELOPMENT   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKANEDIOL DERIVATIVE;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030605166     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01767-4     Document Type: Article

References (23)

1. 1. Reviews: (a) Oishi T.; Nakata, T. Acc. Chem. Res. 1984, 17, 338.
2. (b) Reetz, M. T. Angew. Chem., Int. Ed. Engl. 1984, 23, 556.
3. (c) Bartlett, P. A. Tetrahedron 1980, 36, 3.
4. (d) Asymmetric Synthesis; Morrison, J. D., Ed.; Academic Press: New York, Vol. 2, 1983 and Vol. 3, 1984.
5. (e) Hoveyda, A. H.; Evans, D. A.; Fu, G. C. Chem. Rev. 1993, 93, 1307.
6. 2. (a) Molander, G. A.; Bobbitt, K. L. J. Am. Chem. Soc. 1993, 115, 7517.
7. (b) Molander, G. A.; Haar, J. P., Jr. Ibid. 1993, 115, 40.
8. (c) Panek, J.; Yang, Y. Ibid. 1991, 113, 6594.
9. (d) Erker, G.; Soana, F.; Betz, P.; Werner, S.; Kruger, C. Ibid. 1991, 113, 565.
10. (e) Teerawutgulrag, A.; Thomas, E. J. Chem. Soc., Perkin Trans, 1 1993, 2863.
11. (f) Fang, J.-M.; Chang, C.-J. Ibid. 1989, 1787.
12. (g) Uemura, M.; Minami, T.; Hirotsu, K.; Hayashi, Y. J. Org. Chem. 1989, 54, 469.
13. (h) Tamura, R.; Watabe, K-I.; Katayama, H.; Suzuki, H.; Yamamoto, Y. Ibid. 1990, 55, 408.
14. (i) Denmark, S. E.; Marple, L. K. Ibid. 1990, 55, 1984.
15. (j) Uemura, M.; Minami, T.; Hirotsu, K.; Hayashi, Y. Ibid. 1989, 54, 469.
16. (k) Tamai, Y.; Koike, S.; Ogura, A.; Miyano, S. J. Chem. Soc., Chem. Commun. 1991, 799.
17. 3. Zhang, H.-C.; Costanzo, M. J.; Maryanoff, B. E. Tetrahedron Lett., 1994, 35, 4891.
18. 4. For related examples of bicyclic chelation control, see: (a) Carey, J. S.; Thomas, E. J. Tetrahedron Lett. 1993, 34, 3935.
19. (b) Roush, W. R.; Bannister, T. D.; Wendt, M. D. Ibid. 1993, 34, 8387.
20. (c) Ref. 2a.
21. (d) Ref. 2k.
22. 4). The volatiles were removed in vacuo and the residue was separated by preparative TLC (EtOAc-hexane, 1:4) to give 4, as a mixture of anti and syn diols.
23. 3). Both AB quartets centered around δ 3.75 but had no overlapping of peaks due to the variation in the chemical shift difference between the pair of doublets in the AB quartets for the two isomers (anti isomer: Δδ = 0.28 ppm, J = 13.3 Hz; syn isomer: Δδ = 0.57 ppm, J = 13.2 Hz).