The use of polymer-bound triphenylphosphine in the stereochemical inversion of secondary alcohols

Combinatorial Chemistry and High Throughput Screening

Volumn 3, Issue 2, 2000, Pages 103-106

  White, J M ^a   Tunoori, A R ^a   Dutta, D ^a   Georg, G I ^a  

^a UNIVERSITY OF KANSAS   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

POLYMER; TRIPHENYLPHOSPHINE;

CHEMICAL REACTION; FILTRATION; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION TIME; REVIEW; STEREOCHEMISTRY;

EID: 0034043901     PISSN: 13862073     EISSN: None     Source Type: Journal    
DOI: 10.2174/1386207003331706     Document Type: Review

References (13)

1. Tunoori, A. R.; Dutta, D.; Georg, G. Tetrahedron Lett. 1998, 39, 8751-8754.
2. Hughes, D. L. In Organic Reactions; Joyce, R. M., Ed.; Wiley: New York, 1992; Vol. 42; pp 335-656.
3. Hughes, D. L. Org. Prep. Proced. Int. 1996, 28, 127-164.
4. Drewry, D. H.; Coe, D. M.; Poon, S. Med. Res. Rev. 1999, 19, 97-148.
5. Janda, K. D.; Wentworth, P.; Vandersteen, A. M. J. Chem. Soc., Chem. Commun. 1997, 8, 759-760.
6. Amos, R. A.; Emblidge, R. W.; Havens, N. J. Org. Chem. 1983, 48, 3598-3600.
7. Kiankarimi, M.; Lowe, R.; McCarthy, J.; Whitten, J. Tetrahedron Lett. 1999, 40, 4497-4500.
8. Starkey, G. W.; Parlow, J. J.; Flynn, D. L. Bioorg. Med. Chem. Lett. 1998, 8, 2385-2390.
9. 13C NMR, and mass spectrometry along with optical rotation. All starting materials were obtained from Aldrich Chemical Co. with the exception of the polymer-bound triphenylphosphine which was purchased from Fluka (catalogue no. 93093).
10. Martin, S. F.; Dodge, J. A. Tetrahedron Lett. 1991, 32, 3017-3020.
11. Saiah, M.; Bessodes, M.; Antonakis, K. Tetrahedron Lett. 1992, 33, 4317-4320.
12. Tsunoda, T.; Yamamiya, Y.; Kawamura, Y.; Ito, S. Tetrahedron Lett. 1995, 36, 2529-2530.
13. Conflicting information was issued in two independent reports by Saiah et al. and Tsunoda et al. (ref 11 and 12, respectively) regarding entry 3 (Table 2). The former group reported 61%, and the later reported 0% yield. Our results confirmed the Tsunoda results for both the standard and polymer-bound Mitsunobu conditions. Furthermore, our results for entry 2 (Table 2) were also in disagreement with Saiah who reported 67% yield. Although we were able to obtain the compound, only a 25% yield for both the standard and the Mitsunobu conditions using polymer-bound triphenylphosphine was obtained.