Methylaluminum bis(2, 6-di-tert-butyl-4-methylphenoxide) as a protecting group for multifunctional molecules: Synthetic utility in selective carbonyl reductions

Journal of the American Chemical Society

Volumn 110, Issue 8, 1988, Pages 2650-2652

  Maruoka, Keiji ^a   Araki, Yoshitaka ^a   Yamamoto, Hisashi ^a  

^a NAGOYA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33845278196     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00216a050     Document Type: Article

References (5)

1. Reviews of selective reduction: (a) House, H. O. Modern Synthetic Reaction, 2nd ed.; W. A. Benjamin: New York, NY, 1972. (b) Brown, H. C. Boranes in Organic Chemistry; Cornell University Press: Ithaca, NY, 1972. (c) Walker, E. R. H. Chem. Soc. Rev. 1976, 5, 23. (d) Hajós, C. Sc. A. Complex Hydrides and Related Reducing Agents in Organic Synthesis; Elsevier: New York, 1979. (e) Brown, H. C.; Krishnamurthy, S. Tetrahedron Lett. 1979, 33, 567. (f) Brown, H. C; Krishnamurthy, S. Aldrich. Acta 1979, 12, 3. (g) Hudlický, M. Reductions in Organic Chemistry; Ellis Hoewood Limited: Chichester, England, 1984.
2. Highly selective reduction of sterically less hindered keto group with lithium dibutyl-9-borabicyclo[3.3.1]nonane: Yamamoto, Y.; Toi, H.; Sonoda, A.; Murahashi, S. J. Am. Chem. Soc. 1976, 98, 1965.
3. Selective carbonyl alkylation of a sterically more hindered keto group has been accomplished via chemoselective in situ protection of a less hindered keto group with titanium tetrakis(dialkylamide): Reetz, M. T.; Wenderroth, B.; Pelter, R. J. Chem. Soc., Chem. Commun. 1983, 406. See, also: Reetz, M. T. Top. Curr. Chem. 1982, 106, 1.
4. (a) Maruoka, K.; Itoh, T.; Yamamoto, H. J. Am. Chem. Soc. 1985, 107, 4573. (b) Maruoka, K.; Sakurai, M.; Yamamoto, H. Tetrahedron Lett. 1985, 26, 3853.
5. 4in benzene. See: Stillson, G. H.; Sawyer, D. W.; Hunt, C. K. J. Am. Chem. Soc. 1945, 67, 303.