Synthesis of chiral 13C,77Se-labeled selones

Journal of Organic Chemistry

Volumn 69, Issue 15, 2004, Pages 5150-5152

  Ollivault Shiflett, Morgane ^a   Kimball, David B ^a   Silks, L A ^a  

^a LOS ALAMOS NATIONAL LABORATORY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACETIC ACID; CHEMICAL ANALYSIS; DEMODULATION; SYNTHESIS (CHEMICAL);

CHIRALS; ENOLATE STRUCTURES; QUANTITATION;

ORGANIC COMPOUNDS;

BROMOACETIC ACID; FORMIC ACID; SELENIUM DERIVATIVE; SELONE DERIVATIVE; UNCLASSIFIED DRUG; CARBON; ISOTOPE;

ARTICLE; CHIRALITY; ISOTOPE LABELING; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS; SYNTHESIS; CHEMICAL STRUCTURE; CHEMISTRY;

CARBON ISOTOPES; ISOTOPES; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; SELENIUM COMPOUNDS;

EID: 3543023886     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo049747o     Document Type: Article

References (17)

1. Wu, R.; Hernandez, G.; Dunlap, R. B.; Odom, J. D.; Martinez, R. A.; Silks, L. A. Trends Org. Chem. 1998, 7, 105.
2. Silks, L. A.; Dunlap, R. B.; Odom, J. D. J. Am. Chem. Soc. 1990, 112, 4979.
3. Wu, R.; Odom, J. D.; Dunlap, R. B.; Silks, L. A. Tetrahedron: Asymmetry 1999, 10, 1465.
4. Hedenstrom, E.; Nguyen, B. V.; Silks, L. A. Tetrahedron: Asymmetry 2002, 13, 835.
5. Li, Z.; Wu, R.; Michalczyk, R.; Dunlap, R. B.; Odom, J. D.; Silks, L. A. P. J. Am. Chem. Soc. 2000, 122, 386.
6. Kimball, D. B.; Michalczyk, R.; Moody, E.; Ollivault-Shiflett, M.; De Jesus, K.; Silks, L. A. P. J. Am. Chem. Soc. 2003, 125, 14666.
7. Se-C for selenocarbonyls range from 220 to 242 Hz. The decrease in the value of the coupling constant indicates less s character in the bonding system, which results in a longer bond.
8. For the construction of the valinol-derived oxazoline: Meyers, A. I.; Collington, E. W. J. Am. Chem. Soc. 1970, 92, 6676. Also see: Leonard, W. R.; Romine, J. L.; Meyers, A. I. J. Org. Chem. 1991, 56, 1961.
9. For the construction of the valinol-derived oxazoline: Meyers, A. I.; Collington, E. W. J. Am. Chem. Soc. 1970, 92, 6676. Also see: Leonard, W. R.; Romine, J. L.; Meyers, A. I. J. Org. Chem. 1991, 56, 1961.
10. (a) Meyer, J. Z. Elektrochem. Angew. Phys. Chem. 1909, 15, 506.
11. (b) Schierz, E. R. J. Am. Chem. Soc. 1923, 45, 447.
12. Peng, J.; Barr, M. E.; Ashburn, D. A.; Odom, J. D.; Dunlap, R. B.; Silks, L. A. J. Org. Chem. 1994, 59, 4977.
13. 77Se NMR shows a single doublet at 550.2 ppm (the apparent minor doublet at 680 ppm has J = 140 Hz and cannot be from a selenocarbonyl). Dale, J. A.; Dull, D. L.; Mosher, H. S. J. Org. Chem. 1969, 34, 2543.
14. (a) Gravestock, M. B.; Knight, D. W.; Lovell, J. S.; Thornton, S. R. J. Chem. Soc., Perkin Trans. 1 1999, 3143.
15. (b) Miller, R. D.; Theis, W.; Heilig, G.; Kirchmeyer, S. J. Org. Chem. 1991, 56, 1453.
16. Peng, J.; Barr, M. E.; Ashburn, D. A.; Lebioda, L.; Garber, A. R.; Martinez, R. A.; Odom, J. D.; Dunlap, R. B.; Silks, L. A. J. Org. Chem. 1995, 60, 5540.
17. For the unlabeled compound, lit. bp 81-83 °C, 0.6 mm: Bennington, F.; Morin, R. D. J. Org. Chem. 1981, 26, 194.