Enantioselective alkylation of aldehydes with chiral organomagnesium amides (COMAs)

Organic Letters

Volumn 4, Issue 21, 2002, Pages 3553-3556

  Yong, Kelvin H ^a   Taylor, Nicholas J ^a   Chong, J Michael ^a  

^a UNIVERSITY OF WATERLOO   (Canada)

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EID: 0037914044     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0258132     Document Type: Article

References (21)

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2. Reviews: (a) Solladié, G. In Asymmetric Synthesis; Morrison, J. D., Ed.; Academic Press: New York, 1983: Vol. 2, pp 157-199,
3. (b) Huryn, D. M. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds; Pergamon: Oxford, 1991; Vol. I, part I, pp 49-75.
4. Recent examples: (a) Weber, B.; Seebach, D. Tetrahedron 1994, 50, 6117-6128.
5. (b) Nakajima, M.; Tomioka, K.; Koga, K. Tetrahedron 1993, 49, 9751-9758.
6. (c) Knollmüller, M.; Ferencic, M.; Gärtner, P. Tetrahedron: Asymmetry 1999, 10, 3969-3975.
7. Disclosed, in part, in: Chong, J. M.; Yong, K. H. Asymmetric Alkylation of Aldehydes with Chiral Organomagnesium Amides; PacifiChem 2000, Honolulu, HI, 2000.
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9. It was suggested that the use of alkyl(amido)magnesium compounds as "asymmetric induction reagents" would be studied, but results have not been reported: Henderson, K. W.; Allan, J. F.; Kennedy, A. R. J. Chem. Soc., Chem. Commun. 1997, 1149-1150.
10. Very recently, the enantioselective 1,4-addition of organomagnesium amides derived from bisoxazolines to enamidomalonates was described: Sibi, M. P.; Asano, Y. J. Am. Chem. Soc. 2001, 123, 9708-9709.
11. Related chiral magnesium bisamides have been reported to be effective for enantioselective deprotonations: (a) Henderson, K. W.; Kerr, W. J.; Moir, J. H. J. Chem. Soc., Chem. Commun. 2000, 479-480.
12. (b) Henderson, K. W.; Kerr, W. J., Moir, J. H. Tetrahedron 2002, 58, 4573-4587.
13. Rossiter, B. E.; Eguchi, M.; Miao, G.; Swingle, N M.; Hemandez, A. E.; Vickers, D.; Medich, J.; Marr, J.; Heinis, D. Tetrahedron 1993, 49, 965-986.
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15. See Supporting Information for details.
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