Mukaiyama Aldol Reactions Catalyzed by Zirconocene Bis(triflate) Complexes: Stereochemistry and Mechanisms for C-C Bond Formation

Journal of Organic Chemistry

Volumn 63, Issue 6, 1998, Pages 1885-1892

  Lin, Shuqiong ^a   Bondar, Georgiy V ^a   Levy, Christopher J ^a   Collins, Scott ^a  

^a UNIVERSITY OF WATERLOO   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0038018757     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo971803g     Document Type: Article

References (24)

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3. Jaquith, J. B.; Guan, J.; Wang, S.; Collins, S. Organometallics 1995, 14, 1079 and references therein.
4. Jaquith, J. B.; Levy, C. J.; Bondar, G. V.; Collins, S. Organometallics, in press.
5. For a review of synthetic applications see: Reetz, M. T. Angew. Chem., Int. Ed. Engl. 1984, 23, 556.
6. For relevant mechanistic work see: (a) Reetz, M. T.; Raguse, B.; Seitz, T. Tetrahedron 1993, 49, 8561 and references therein. (b) Keck, G. E.; Castellino, S. J. J. Am. Chem. Soc. 1986, 108, 3847.
7. For relevant mechanistic work see: (a) Reetz, M. T.; Raguse, B.; Seitz, T. Tetrahedron 1993, 49, 8561 and references therein. (b) Keck, G. E.; Castellino, S. J. J. Am. Chem. Soc. 1986, 108, 3847.
8. Hollis, T. K.; Bosnich, B. J. Am. Chem. Soc. 1995, 117, 4570 and references therein.
9. Heathcock, C. H. In Asymmetric Synthesis; Morrison, J. D., Ed.; Academic Press: New York, 1984; Vol. 3, pp 115-118 and references therein.
10. A number of other signals were present that might be assigned to this intermediate, but their low intensity precluded unambiguous identification.
11. It is quite possible that TMSOTf is also a catalyst for this isomerization process in nitroalkane solvents as the rate of isomerization qualitatively increased as the amount of TMSOTf increased.
12. (a) Kobayashi, S.; Uchiro, H.; Shiina, I.; Mukaiyama, T. Tetrahedron 1993, 49, 1761.
13. (b) Carreira, E. M.; Singer, R. A. Tetrahedron Lett. 1994, 35, 4323.
14. (c) Denmark, S. E.; Chen, C. T. Ibid. 1994, 35, 4327.
15. Qualitatively similar results were observed using 2 and PhCHO. However, quantitation was not possible due to the formation of syn and anti diastereomers, which were not adequately separated by GC.
16. 3 as a catalyst with simple aldehyde substrates gave rise to aldol products in <20% ee. Collins, S. Unpublished results.
17. 5b
18. 2SiOTf.
19. (a) Siedle, A. R.; Newmark, R. A.; Glenson, W. B.; Lamanna, W. M. Organometallics 1990, 9, 1290.
20. (b) Thewalt, U.; Klein, H. P. Z. Kristallogr. 1980, 153, 307.
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22. b) Ireland, R. E.; Mueller, R. H.; Willard, A. K. J. Am. Chem. Soc. 1976, 98, 2868.
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