Stereocontrolled polyol synthesis via C-H insertion reactions of silicon tethered diazoacetates

Tetrahedron Letters

Volumn 39, Issue 28, 1998, Pages 5109-5112

  Kablean, Susie N ^a   Marsden, Stephen P ^a   Craig, Alison M ^b  

^a IMPERIAL COLLEGE LONDON   (United Kingdom)

^b JEALOTT S HILL RESEARCH STATION   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ACETIC ACID DERIVATIVE; AZO COMPOUND; CYCLOPENTANE DERIVATIVE; ESTER; POLYOL; RHODIUM; SILANE DERIVATIVE; SILICON;

ARTICLE; CATALYSIS; CHEMICAL BOND; CHEMICAL REACTION; CYCLIZATION; DIASTEREOISOMER; OXIDATION REDUCTION REACTION; STEREOCHEMISTRY; SYNTHESIS;

EID: 0032500148     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)00938-1     Document Type: Article

References (10)

1. 1. Pang, W.-K.; Marsden, S. P., unpublished results
2. 2. For a review of diazocarbonyl chemistry, see: Ye, T; McKervey, M. A. Chem. Rev. 1993, 93, 1091
3. 3. Jones, G. R.; Landais, Y. Tetrahedron 1996, 52, 7599
4. 4. Bols, M.; Skrydstrup, T. Chem. Rev. 1995, 95, 1253
5. 5. In the C-H insertion reaction of menthyl diazoacetoacetate, Doyle observed the formation of a trans-fused butyrolactone with the acetyl side chain situated trans to the adjacent ring junction, as determined by the relevant J values (10.7 and 12.4 Hz respectively). Doyle, M. P.; Westrum, L.J.; Wolthuis, W. N. E.; See, M. M.; Boone, W. P.; Bagheri, V.; Pearson, M. M. J. Am. Chem. Soc. 1993, 115, 958
6. 6. Fronda, A.; Krebs, F.; Daucher, B.; Werle, T.; Maas, G. J. Organomet. Chem. 1992, 424, 253
7. 7. The stereochemistry of all bicyclic oxasilacyclopentanes formed has been assigned by analysis of the J values for the protons at the ring fusion, and between the ring fusion and 5-ring substituent, by comparison with the structure in reference 5. Representative J values: 3b (10.0, 12.0 Hz), 3e (10.0, 11.6 Hz), 7 (10.9, 12.1 Hz), 10 (10.3, 12.3Hz), 13a (10.3, 12.5 Hz), 13b (10.0, 12.5 Hz).
8. 8. Taber, D. F.; Ruckle, R. E. J. Am. Chem. Soc. 1986, 108, 7686
9. 9. For a recent review of advances in asymmetric catalysis in carbenoid chemistry, see: Doyle, M. P.; McKervey, M. A. Chem. Commun. 1997, 983
10. 10. We thank Dr A. J. P. White and Professor D. J. Williams of this department for this determination.