Demonstration of a phosphazirconocene as a catalyst for the ring opening of epoxides with TMSCI

Organic Letters

Volumn 5, Issue 14, 2003, Pages 2543-2545

  Wang, Li Sheng ^a,b   Hollis, T Keith ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b Maxdem Inc   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CHLOROHYDRIN DERIVATIVE; EPOXIDE; IRON DERIVATIVE; ZIRCONIUM DERIVATIVE; ZIRCONOCENE;

ARTICLE; CATALYSIS; CATALYST; REACTION ANALYSIS; REACTION TIME; RING OPENING; STEREOCHEMISTRY; SYNTHESIS;

EID: 0141519627     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol034816r     Document Type: Article

References (12)

1. Garrett, C. E.; Fu, G. C. J. Org. Chem. 1997, 62, 4534-4535.
2. Andrews, G. C.; Crawford, T. C.; Contillo, L. G., Jr. Tetrahedron Lett. 1981, 22, 3803-3806.
3. Nief, F.; Mathey, F.; Richard, L. Organometallics 1988, 7, 921-926.
4. For recent examples of phosphorous-based nucleophilic catalyses, see: Zhu, G.; Chen, Z.; Jiang, Q.; Xiao, D.; Cao, P.; Zhang, X. J. Am. Chem. Soc. 1997, 119, 3836-3837. Vedejs, E.; Dauglis, O. J. Am. Chem. Soc. 1999, 121, 5813-5814.
5. For recent examples of phosphorous-based nucleophilic catalyses, see: Zhu, G.; Chen, Z.; Jiang, Q.; Xiao, D.; Cao, P.; Zhang, X. J. Am. Chem. Soc. 1997, 119, 3836-3837. Vedejs, E.; Dauglis, O. J. Am. Chem. Soc. 1999, 121, 5813-5814.
6. Nucleophilic catalysis: Tao, B.; Ruble, C.; Hoic, D. A.; Fu, G. C. J. Am. Chem. Soc. 1999, 121, 5091-5092.
7. Denmark, S. E.; Barsanti, P. A.; Wong, K.-T.; Stavenger, R. A. J. Org. Chem. 1998, 63, 2428-2429.
8. Ready, J. M.; Jacobsen, E. N. J. Am. Chem. Soc. 1999, 121, 6086-6087.
9. McCleland, B. W.; Nugent, W. A.; Finn, M. G. J. Org. Chem. 1998, 63, 6656-6666.
10. 13C sidebands and authentic samples.
11. For an example of similar results, see: Afonso, C. A. M.; Vieira, N. M. L.; Motherwell, W. B. Synlett 2000, 382-384.
12. Garrett and Fu employed 5 mol % vs our 1 mol % for comparable rates; see ref 1.