A rationally designed chiral auxiliary for hydroxyalkyl radicals leads to exceptional ρ-stereocontrol

Tetrahedron Letters

Volumn 38, Issue 38, 1997, Pages 6647-6650

  Garner, Philip ^a   Anderson, James T ^a  

^a CASE WESTERN RESERVE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

HYDROXYL RADICAL; TETRAHYDROPYRAN DERIVATIVE;

ARTICLE; CHEMICAL MODIFICATION; CHEMICAL REACTION; HYDROLYSIS; SYNTHESIS; TEMPERATURE;

EID: 0030828429     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)01580-3     Document Type: Article

References (9)

1. Curran, D.P.; Porter, N.A.; Giese, B. Stereochemistry of Radical Reactions, VCH, Weinheim, 1996.
2. Garner P.P., Cox P.B., Klippenstein S.J. J. Am. Chem. Soc. 117:1995;4183-4184.
3. Garner P., Leslie R., Anderson J.T. J. Org. Chem. 61:1996;6754-6755.
4. Our work on t-butyl substituted auxiliaries actually involved the antipodes of the structures shown in this paper. However, the D-series has been depicted to facilitate comparisons with the structures from our previous publications.
5. Crimmins M.T., Al-awar R.S., Vallin I.M., Hollis W.G., O'Mahony R., Lever J.G., Bankaitis-Davis D.M. J. Am. Chem. Soc. 118:1996;7513-7528.
6. (a) Hanson, R.M.; Sharpless, K.B. J. Org. Chem. 1986, 51, 1922-1925;
7. (b) The enantiomeric excess (ee) of 5 was determined via its Mosher ester derivative: Dale, J.A.; Dull, D.A.; Mosher, H.S. J. Org. Chem. 1969, 34, 2543-2549.
8. Compounds 5 and 6 are known. See: Konoike, T.; Hayashi, T.; Araki, Y. Tetrahedron Asymmetry 1994, 5, 1559-1566, and reference 17 cited therein.
9. 3N. Details of this method for Barton ester formation will be reported separately.