A simple, highly regioselective, one-pot stereoselective synthesis of tertiary α-hydroxyesters: a tandem oxidation/benzilic ester rearrangement

Tetrahedron Letters

Volumn 47, Issue 34, 2006, Pages 6049-6052

  Marques, Carolina Sílva ^a   Moura, Nuno ^a   Burke, Anthony J ^a  

^a UNIVERSITY OF ÉVORA   (Portugal)

Author keywords

[No Author keywords available]

Indexed keywords

BENZILIC ACID DERIVATIVE; ESTER DERIVATIVE; KETONE DERIVATIVE;

ARTICLE; OXIDATION; STEREOCHEMISTRY; SYNTHESIS;

EID: 33745989231     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2006.06.107     Document Type: Article

References (22)

1. White J.M., and Ohira S. J. Org. Chem. 51 (1986) 5492
2. Vedejs E., Ahmad S., Larsen S.D., and Westwood S. J. Org. Chem. 52 (1987) 3937
3. Senanayake C.H., Fang K., Grover P., Bakale R.P., Vandenbossche C.P., and Wald S.A. Tetrahedron Lett. 40 (1999) 819
4. Subrahmanyam D., Sarma V.M., Venkateswarlu A., Sastry T.V.R.S., Kulakarni A.P., Rao D.S., and Reddy K.V.S.R.K. Biorg. Med. Chem. 7 (1999) 2013
5. Barker M., Clackers M., Demaine D.A., Humphreys D., Johnston M.J., Jones H.T., Pacquet F., Pritchard J.M., Salter M., Shanahan S.E., Skone P.A., Vinader V.M., Uings I., McLay I.M., and Macdonald S.J.F. J. Med. Chem. 48 (2005) 4507
6. Loupy A., and Monteux D.A. Tetrahedron 65 (2002) 1541
7. Fennie M.W., DiMauro E.F., O'Brien E.M., Venkatachalam A., and Kozlowski M.C. Tetrahedron 61 (2005) 6249
8. Wang Z., Xu G., Wang D., Pierce M.E., and Confalone P.N. Tetrahedron Lett. 41 (2000) 4523
9. Juhl K., Gathergood N., and Jørgensen K.A. Chem. Commun. (2000) 2211
10. Casiraghi G., Bigi F., Casnati G., Sartori G., Soncini P., Fava G.G., and Belicchi M.F. J. Org. Chem. 53 (1988) 1779
11. Nicolaou K.C., Yue E.W., La Greca S., Nadine A., Yang Z., Leresche J.E., Tsuri T., Naniwa Y., and De Riccardis F. Chem. Eur. J. 1 (1995) 467
12. Burke, A. J. Ph.D. Thesis, National University of Ireland, 1993.
13. Burke A.J., Schmalle H.W., Brady B.A., and O'Sullivan W.I. Acta Cryst. C56 (2000) 484
14. The major isomer was established to be the anti-isomer from a derivatisation study on a glycolic acid precursor of known relative configuration (Ref. 12).
15. March J. Advanced Organic Chemistry. 4th ed. (1992), Wiley Interscience p 1080
16. This type of reaction has previously been reported for a cortisone α-diketone derivative:. Lewbart M.L., and Mattox V.R. J. Org. Chem. 28 (1963) 1773
17. Brady B.A., Geoghegan M., and O'Sullivan W.I. J. Chem. Soc. Perkin Trans. 1 (1989) 1557
18. Weitz E., and Scheffer A. Ber. 54 (1921) 2327
19. Carde L., Davies H., Geller T.P., and Roberts S.M. Tetrahedron Lett. 41 (1999) 5421
20. Xu L., Li C., Xia C., and Zhao P. Tetrahedron Lett. 45 (2004) 1
21. Kolbe H.C., Finn M.G., and Sharpless K.B. Angew. Chem., Int. Ed. 40 (2001) 2005
22. In fact, the preceding ring-opening reaction is a classic example of a click chemical process (Ref. 21).