An efficient method for deprotection of acetals

Tetrahedron Letters

Volumn 39, Issue 19, 1998, Pages 3091-3092

  Saravanan, P ^a   Chandrasekhar, M ^a   Anand, R Vijaya ^a   Singh, Vinod K ^a  

^a INDIAN INSTITUTE OF TECHNOLOGY KANPUR   (India)

Author keywords

[No Author keywords available]

Indexed keywords

ACETAL DERIVATIVE;

ARTICLE; CHIRALITY; SYNTHESIS; TECHNIQUE;

EID: 0032493003     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)00366-9     Document Type: Article

References (11)

1. 1. Saravanan, P.; Raina, S.; Sambamurthy, T.; Singh, V. K. J. Org. Chem. 1997, 62, 2669.
2. 2. (a). Murrer, B. A.; Brown, J. M. Synthesis 1979, 350.
3. (b). Schurig, V.; Koppenhoefer, B.; Buerkle, W. J. Org. Chem. 1980, 45, 538.
4. (c). Kabat, M. M.; Kiegiel, J.; Cohen, N.; Toth, K.; Wovkulich, P. M.; Uskokovic, M. R. J. Org. Chem. 1996, 61, 118 and references cited therein.
5. 3. For some recent methods for deprotection of acetals, see: (a). Sen, S. E.; Roach, S. L.; Boggs, J. K.; Ewing, G. J.; Magrath, J. J. Org. Chem. 1997, 62, 6684.
6. (b). Gautier, E. C. L.; Graham, A. E.; McKillop, A.; Standen, S. P.; Taylor, R. J. K. Tetrahedron Lett. 1997, 38, 1881.
7. (c). Mandal, P. K.; Dutta, P.; Roy, S. C. Tetrahedron Lett. 1997, 38, 7271.
8. 2 has not been used in literature for deprotection of acetals. However, it has been used for preparation of acetals. For references, see: (a). Matsumura, K.; Aono, T. Eur. Pat. Appl. 1997, EP 82-305053 820924; CA 99: 71129.
9. (b). Satoh, J. Y.; Yokoyama, C. T.; Haruta, A. M. Chem Lett. 1974, 1521.
10. 3 solution, brine, and dried. Solvent removal and purification over silica gel gave pure product.
11. 2O also cleaved TBDMS ether in an efficient manner. For example, decanol-TBDMS ether was cleaved in 30 min. into alcohol in 92% yield. Similarly, decanol THP ether was cleaved in 90 min. into the alcohol in 50% yield.