Highly chemo-, diastereo-, and enantioselective reduction of 1,2-dialkyl-3-aryl-1,3-diketones for preparation of aldol-type compounds

Organic Letters

Volumn 3, Issue 21, 2001, Pages 3421-3424

  Ohtsuka, Yuhki ^a   Koyasu, Kiichirou ^a   Miyazaki, Daichi ^a   Ikeno, Taketo ^a   Yamada, Tohru ^a  

^a KEIO UNIVERSITY   (Japan)

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EID: 0000869163     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol016676w     Document Type: Article

References (15)

1. (a) Heathcock, C. H. Comprehensive Organic Synthesis; Heathcock, C. H., Ed.; Pergamon Press: Oxford, 1991; Vol. 2, p 133.
2. (b) Mukaiyama, T. Org. React. 1982, 28, 203.
3. For recent examples of the total synthesis of natural products, see: (a) Wakabayashi, T.; Mori, K.; Kobayashi, S. J. Am. Chem. Soc. 2001, 123, 1372.
4. (b) Evans, D. A.; Fitch, D. M.; Smith, T. E.; Cee, V. J. J. Am. Chem. Soc. 2000, 122, 10033.
5. (c) Ma, D.; Sun, H. Tetrahedron Lett. 2000, 41, 1947.
6. For recent examples of the total synthesis of natural products, see: (a) Paterson, I.; Davies, R. D. M.; Marquez, R. Angew. Chem., Int. Ed. 2001, 40, 603.
7. (b) Shing, T. K. M.; Jiang, Q. J. Org. Chem. 2000, 65, 7059.
8. (c) Davenport, R. J.; Regan, A. C. Tetrahedron Lett. 2000, 41, 7622.
9. (a) Carreira, E. M. Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds: Springer, Heidelberg, 1999; Vol. 3, p 998.
10. (b) Machajewski, T. D.; Wong, C.-H. Angew. Chem., Int. Ed. 2000, 39, 1352.
11. Ohtsuka, Y.; Koyasu, K.; Ikeno.; T. Yamada, T. Org. Lett. 2001, 3, 2543.
12. Sugi, K. D.; Nagata, T.; Yamada, T.; Mukaiyama, T. Chem. Lett. 1996, 1081.
13. To reduce the excess hydride in the catalytic system and avoid noncatalytic reduction further, four portions of the 0.1 equiv of the premodified borohydride were successively added at 2 h intervals to the reaction mixture.
14. Nagata, T.; Sugi, K. D.; Yamada, T.; Mukaiyama, T. Synlett 1996, 1076.
15. Nagata, T.; Sugi, K. D.; Yorozu, K.; Yamada, T.; Mukaiyama, T. Catal. Surv. Jpn. 1998, 2, 47.