Sc(OTf)3, an efficient catalyst for formation and deprotection of geminal diacetates (acylals); Chemoselective protection of aldehydes in presence of ketones

Synlett

Volumn , Issue 8, 1998, Pages 849-850

  Aggarwal, Varinder K ^a   Fonquerna, Silvia ^a   Vennall, Graham P ^a  

^a UNIVERSITY OF SHEFFIELD   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 26844441037     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1998-1799     Document Type: Article

References (12)

1. Gregory, M. J. J. Chem. Soc. (B) 1970, 1201.
2. Pinnick, H. W.; Kochhar, K. S.; Bal, B. S.; Deshpande, R. P.; Rajadhyaksha, S. N. J. Org. Chem. 1983, 48, 1765.
3. Olah, G. A.; Mehrotra, A. K. Synthesis 1982, 962.
4. Scriabine, I. Bull. Chem. Soc. Fr. 1961, 1194.
5. Michie, J. K.; Miller, J. A. Synthesis 1981, 824.
6. Gigante, B.; Pereira, C.; Marcelo-Curto, M. J.; Carreyre, H.; Perot, G.; Guisnet, M. Synthesis 1995, 1077.
7. Sarma, J. C.; Deka, N.; Kalita, D. J.; Borah, R. J. Org. Chem. 1997, 62, 1563.
8. Aggarwal, V.K.; Vennall, G.P. Davey, P.N.; Newman, C. Tetrahedron Lett. 1998, 39, 1997.
9. 3] has been used as a catalyst for acetalisation of carbonyl compounds: Ishihara, K.; Karumi, Y.; Kubota, M.; Yamamoto, H. Synlett 1996, 839.
10. For examples of protection of aldehydes as acetals in the presence of ketones see: (a) Tolstikov, G. A.; Miftakhov, M. S.; Akhmetvaleev, R. R.; Balezina, G. G.; Valeev, F. A. Zh. Org. Khim. 1990, 26, 2156-2165.
11. (b) Tolstikov, G. A.; Galin, F. Z.; Ignatyuk, V. K.; Makaev, F. Z.; Yulmukhametova, N. A.; Abdrakhimova, S. A.; Khalilov, L. M.; Sultanova, V. S. Zh. Org. Khim. 1991, 27, 335-340.
12. (c) Hadj-Abo, F.; Hesse, M. Helv. Chim. Acta 1992, 75, 1834-1839.