Catalytic asymmetric synthesis of Syn-aldol products from intermolecular C-H insertions between allyl silyl ethers and methyl aryldiazoacetates

Organic Letters

Volumn 1, Issue 3, 1999, Pages 383-385

  Davies, Huw M L ^a   Antoulinakis, Evan G ^a   Hansen, Tore ^a  

^a UNIVERSITY AT BUFFALO   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000073480     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol9905809     Document Type: Article

References (20)

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2. (b) Evans, D. A. Aldrichimica Acta 1982, 15, 23.
3. For a comprehensive review of catalytic enantioselective aldol reactions, see: Nelson, S. G. Tetrahedron: Asymmetry 1998, 9, 357.
4. For representative examples of intermolecular C-H insertions, see: (a) Scott, L. T.; DeCicco, G. J. J. Am. Chem. Soc. 1974, 96, 322.
5. (b) Ambramovitch, R. A.; Roy, J. J. Chem. Soc., Chem. Commun. 1965, 542.
6. (c) Adams, J.; Poupart, M.-A.; Greainer, L.; Schaller, C.; Quimet, N.; Frenette, R. Tetrahedron Lett. 1989, 30, 1749.
7. (d) Demonceau, A.; Noels, A. F.; Hubert, A. J.; Teyssie, P. J. Chem. Soc., Chem. Commun. 1981, 688.
8. (e) Demonceau, A.; Noels, A. F.; Hubert, A. J.; Teyssie, P. Bull. Soc. Chim. Belg. 1984, 93, 945.
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11. (h) Callott, H. J.; Metz, F. Nouv. J. Chim. 1985, 9, 167.
12. Evans, D. A.; Kozlowski, M. C.; Murry, J. A.; Burgey, C. S., Campos, K. R.; Connell, B. T.; Staples, R. J. J. Am. Chem. Soc. 1999, 121, 669.
13. Lutzen, A.; Koll, P. Tetrahedron: Asymmetry 1997, 8, 1193.
14. (a) Davies, H. M. L. Curr. Org. Chem. 1998, 2, 463.
15. (b) Davies, H. M. L. Aldrichimica Acta 1997, 30, 107.
16. Davies, H. M. L.; Hansen, T. J. Am. Chem. Soc. 1997, 119, 9075.
17. Davies, H. M. L.; Bruzinski, P. R.; Fall, M. J. Tetrahedron Lett. 1996, 37, 4133.
18. 1H NMR. Enantiomeric excesses were determined by HPLC using a Chiralcel OD column and 2-propanol in hexane as the eluent.
19. β (J = 3.4 Hz) to the literature value (J = 3.7 Hz) (Guanti, G.; Banfi, L.; Riva, R. Tetrahedron 1995, 51, 10343.). Syn stereochemistry was assigned to the other C-H insertion products, assuming a similar mode of C-H insertion for all the substrates.
20. 4.