Chemoselective in situ protection of aldehydes and ketones using titanium tetrakis(dialkylamides)

Journal of the Chemical Society, Chemical Communications

Volumn , Issue 8, 1983, Pages 406-408

  Reetz, Manfred T ^a   Wenderoth, Bernd ^a   Peter, Roland ^a  

^a PHILIPPS UNIVERSITY MARBURG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 37049112125     PISSN: 00224936     EISSN: None     Source Type: Journal    
DOI: 10.1039/c39830000406     Document Type: Article

References (11)

1. J. F. W. McOmie, ‘Protective Groups in Organic Chemistry,’ Plenum Press, New York, 1973.
2. T. W. Greene, ‘Protective Groups in Organic Synthesis,’ Wiley, New York, 1981.
3. D. C. Bradley and M. H. Gitlitz, J. Chem. Soc. A, 1969, 980.
4. M. F. Lappert, P. P. Power, A. R. Singer, and R. C. Srivastava, ‘Metal and Metalloid Amides,’ Ellis Horwood, Chichester, 1980.
5. Recently, a method for the in situ protection of aldehydes using lithium morpholide has been described which cannot be utilized for ketones owing to undesired enolization: D. L. Comins and J. D. Brown, Tetrahedron Lett., 1981, 4213.
6. D. L. Comins, J. D. Brown, and N. B. Mantlo, Tetrahedron Lett., 1982, 3979.
7. 4MgCl react selectively with ketones, but the reagents do not discriminate well between two different ketone groups: M. T. Reetz and B. Wenderoth, Tetrahedron Lett., 1982, 5259.
8. Mean bond energies: Ti-O (115 kcal/mol), Ti-N (81 kcal/mol) (1 cal = 4.184 J): M. F. Lappert, D. S. Patil, and J. B. Pedley, J. Chem. Soc., Chem. Commun., 1975, 830.
9. Enamine formation occurs: H. Weingarten and W. A. White, J. Org. Chem., 1966, 31, 4041.
10. M. T. Reetz, Top. Curr. Chem, 1982, 106, 1.
11. B. Weidmann and D. Seebach, Angew. Chem., Int. Ed. Engl., 1983, 22, 31.