Direct asymmetric aldol reactions of acetone using bimetallic zinc catalysts

Organic Letters

Volumn 3, Issue 16, 2001, Pages 2497-2500

  Trost, Barry M ^a   Silcoff, Elliad R ^a   Ito, Hisanaka ^a  

^a STANFORD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACETONE; ZINC;

ARTICLE; CATALYSIS; CHEMISTRY; STEREOISOMERISM;

ACETONE; CATALYSIS; STEREOISOMERISM; ZINC;

EID: 0035833675     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0161211     Document Type: Article

References (29)

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17. For a review of biological methods, see: Machajewski, T. D.; Wong, C.-H. Angew. Chem., Int. Ed. 2000, 39, 1352. For leading references on the use of catalytic antibiotics, see: Turner, J. M.; Bui, T.; Lerner, R. A.; Barbas, C. F., III; List, B. Chem. Eur. J. 2000, 2772. List, B.; Shabat, D.; Barbas, C. F., III; Lerner, R. A. Chem. Eur. J. 2000, 881.
18. For a review of biological methods, see: Machajewski, T. D.; Wong, C.-H. Angew. Chem., Int. Ed. 2000, 39, 1352. For leading references on the use of catalytic antibiotics, see: Turner, J. M.; Bui, T.; Lerner, R. A.; Barbas, C. F., III; List, B. Chem. Eur. J. 2000, 2772. List, B.; Shabat, D.; Barbas, C. F., III; Lerner, R. A. Chem. Eur. J. 2000, 881.
19. For a review of biological methods, see: Machajewski, T. D.; Wong, C.-H. Angew. Chem., Int. Ed. 2000, 39, 1352. For leading references on the use of catalytic antibiotics, see: Turner, J. M.; Bui, T.; Lerner, R. A.; Barbas, C. F., III; List, B. Chem. Eur. J. 2000, 2772. List, B.; Shabat, D.; Barbas, C. F., III; Lerner, R. A. Chem. Eur. J. 2000, 881.
20. Made from the known 2,6-di(hydroxymethyl)-3,5-dimethylphenol (Fitzgerald, J. S. J. Appl. Chem. 1995, 289. Bertz, S. H. Synthesis 1980, 708. Fahrni, C. J.; Pfaltz, A. Helv. Chim. Acta 1998, 81, 491) by sequential treatment with HBr, proline methyl ester, and phenylmagnesium bromide.
21. Made from the known 2,6-di(hydroxymethyl)-3,5-dimethylphenol (Fitzgerald, J. S. J. Appl. Chem. 1995, 289. Bertz, S. H. Synthesis 1980, 708. Fahrni, C. J.; Pfaltz, A. Helv. Chim. Acta 1998, 81, 491) by sequential treatment with HBr, proline methyl ester, and phenylmagnesium bromide.
22. Made from the known 2,6-di(hydroxymethyl)-3,5-dimethylphenol (Fitzgerald, J. S. J. Appl. Chem. 1995, 289. Bertz, S. H. Synthesis 1980, 708. Fahrni, C. J.; Pfaltz, A. Helv. Chim. Acta 1998, 81, 491) by sequential treatment with HBr, proline methyl ester, and phenylmagnesium bromide.
23. The mechanism is related to the amino alcohol catalyzed asymmetric addition of organozinc reagents to aldehydes, cf. Rasmussen, T.; Norrby, P.-O. J. Am. Chem. Soc. 2001, 123, 2464.
24. (a) New compounds have been fully characterized spectroscopically and elemental composition established by high-resolution mass spectrometry and/or combustion analysis.
25. (b) The absolute configurations of the aldol products of entry 1 [Silverman, I. R.; Edington, C.; Eliott J. D.; Johnson, W. S. J. Org. Chem. 1987, 52, 180], entry 2 [ref 5b and 11], entry 3 [ref 11a], entry 6
26. [Carreira, E. M.; Lee, W.; Singer, R. A. J. Am. Chem. Soc. 1995, 117, 3649],
27. and entries 7 and 8 [ref 11b]. The products of entries 5 (ref 5a) and 9 [Grayson, D. H.; Tuite, M. R. J. J. Chem. Soc., Perkin Trans. 1 1986, 2137] are known although the absolute configurations are not identified.
28. (a) Ramachandran, P. V.; Xu, W.-C.; Brown, H. C. Tetrahedron Lett. 1996, 37, 4911;
29. (b) Paterson, I.; Goodman, J. M. Tetrahedron Lett. 1989, 30, 997.