A mechanistic dichotomy in ruthenium-catalyzed propargyl alcohol reactivity: A novel hydrative diyne cyclization

Journal of the American Chemical Society

Volumn 125, Issue 38, 2003, Pages 11516-11517

  Trost, Barry M ^a   Rudd, Michael T ^a  

^a STANFORD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVE; ALKYNE; DIYNE; PROPARGYL ALCOHOL; RUTHENIUM; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CYCLIZATION; HYDRATION; REACTION ANALYSIS; STEREOCHEMISTRY;

ALKYNES; CATALYSIS; CYCLIZATION; CYCLOPARAFFINS; ORGANOMETALLIC COMPOUNDS; PROPANOLS; RUTHENIUM;

EID: 0141645586     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja036410f     Document Type: Article

References (12)

1. Trost, B. M.; Rudd, M. T. J. Am. Chem. Soc. 2002, 124, 4178.
2. Yi, C. S.; Torres-Lubian, J. R.; Liu, N.; Rheingold, A. L.; Guzei, I. A. Organometallics 1998, 17, 1257 and references therein.
3. Trost, B. M.; Rudd, M. T. J. Am. Chem. Soc. 2001, 123, 8862.
4. Trost, B. M.; Rudd, M. T. Org. Lett. 2003, 5, 1467.
5. Ruba, E.; Simanko, W.; Mauthner, K.; Soldouzi, K. M.; Slugovc, C.; Mereiter, K.; Schmid, R.; Kirchner, K Organometallics 1999, 18, 3843.
6. Becker, E.; Ruba, E.; Mereiter, K.; Schmid, R.; Kirchner, K. Organometallics 2001, 20, 3851.
7. Pavlik, S.; Mereiter, K.; Schmid, R.; Kirchner, K. Organometallics 2003, 23, 1771.
8. Diyne-ols cyclize nearly instantaneously with excess water as well.
9. Trost, B. M.; Rudd, M. T. Unpublished results. When the electron-withdrawing group is a terminal methoxycarbonyl substituent, the product is actually isolated as the isomeric pyran.
10. The isomer depicted was confirmed though nOe difference experiments.
11. Kossanyi, J. Bull. Soc. Chim. Fr. 1965, 722.
12. Grover, J. K.; Jones, N. J. Chem. Soc. C 1969, 608.