A facile oxidation/deprotection of electron rich silyl ethers using DDQ

Synlett

Volumn , Issue 8, 1998, Pages 915-917

  Paterson, Ian ^a   Cowden, Cameron J ^a   Rahn, Volker S ^a   Woodrow, Michael D ^a  

^a UNIVERSITY OF CAMBRIDGE   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000346448     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1998-1810     Document Type: Article

References (22)

1. For a recent review on silyl ethers and their selective deprotection, see: Nelson, T. D.; Crouch, R. D. Synthesis 1996, 1031.
2. Kocienski, P. J. Protecting Groups; Thieme: New York, 1994.
3. Greene, T. W.; Wuts, P. G. M. Protective Groups in Organic Synthesis; Wiley-Interscience: New York, 1991.
4. de Vries, E. F. J.; Brussee, J.; van der Gen, A. J. Org. Chem. 1994, 59, 7133.
5. Buckle, D. R. Encyclopaedia of Reagents for Organic Synthesis, VoI 3, Paquette, L. (ed), John Wiley & Sons, Chichester, 1995, 1699.
6. For a review of oxidation reactions using DDQ, see: Walker, D.; Hiebert, J. D. Chem. Rev. 1966, 66, 153.
7. Braude, E. A.; Linstead, R. P.; Wooldridge, K. R. J. Chem. Soc. 1956, 3070.
8. More recently, a reaction catalytic in DDQ has been reported: Cacchi, S.; La Torre, F.; Paolucci, G. Synthesis 1978, 848.
9. Lee-Ruff, E.; Ablenas, F. J. Can. J. Chem. 1989, 67, 699.
10. Caputo, R.; Guaragna, A.; Palumbo, G.; Pedatella, S. J. Org. Chem. 1997, 62, 9369.
11. Wang, W.; Li, T.; Attardo, G. J. Org. Chem. 1997, 62, 6598.
12. The deprotection/oxidation of allylic and benzylic silyl ethers with DDQ has been reported on two occasions that we are aware: (a) Narasimhan, N. S.; Bapat, C. P. J. Chem. Soc. Perkin Trans. I 1984, 1435.
13. (b) Piva, O.; Amougay, A.; Pete, J.-P. Tetrahedron Lett. 1991, 32, 3993.
14. In the first instance, it is likely that the acid-labile trimethylsilyl group is removed before oxidation. In the second case, irradiation with UV light was necessary to give good yields of α,β-unsaturated carbonyl compounds. For a review of other methods of silyl ether oxidation/deprotection, see: Muzart, J. Synthesis, 1993, 11.
15. Yamada, K.; Ojika, M.; Ishigaki, T; Yoshida, Y.; Ekimoto, H.; Arakawa, M. J. Am. Chem. Soc. 1993, 115, 11020.
16. Ojika, M.; Kigoshi, H.; Ishigaki, T.; Tsukada, I.; Tsuboi, T.; Ogawa, T.; Yamada, K. J. Am. Chem. Soc. 1994, 116, 7441.
17. 4), filtered and concentrated. Flash chromatography (20% EtOAc/hexanes) afforded the aldehyde 3 as a colourless oil (314 mg, 92%).
18. 3) 193.8, 159.8, 151.9, 142.3, 134.7, 132.1, 132.0, 131.5, 130.7, 130.7, 128.0, 127.3, 113.6, 94.9, 88.3, 81.0, 79.1, 78.5, 76.8, 76.6, 63.6, 55.7, 55.6, 55.3, 42.6, 39.0, 38.8, 34.9, 34.4, 34.1, 33.6, 32.1, 29.8, 29.6, 28.8, 28.1, 28.0, 27.6, 27.4, 19.8, 18.1, 15.2, 14.2, 13.8, 13.0, 12.0, 10.2.
19. Horita, K.; Yoshioka, T.; Tanaka, T.; Oikawa, Y.; Yonemitsu, O. Tetrahedron 1986, 42, 3021.
20. Tanemura, K.; Suzuki, T.; Horaguchi, T. J. Chem. Soc., Perkin Trans. 1 1992, 2997.
21. (a) Oku, A.; Kinugasa, M.; Kamada, T. Chem Lett. 1993, 165.
22. (b) Tanemura, K.; Suzuki, T.; Horaguchi, T. Bull. Chem. Soc. Jpn. 1994, 67, 290.