Novel enantiomerically pure heteroleptic magnesium complexes for use in enantioselective deprotonation reactions

Synlett

Volumn , Issue 7, 2003, Pages 1017-1021

  Carswell, Emma L ^a   Hayes, Douglas ^b   Henderson, Kenneth W ^a,c   Kerr, William J ^a   Russell, Claire J ^a  

^a UNIVERSITY OF STRATHCLYDE   (United Kingdom)

^b GLAXOSMITHKLINE   (United Kingdom)

^c UNIVERSITY OF NOTRE DAME   (United States)

Author keywords

Asymmetric synthesis; Chirality; Heteroleptic complexes; Magnesium amides

Indexed keywords

AMIDE; BASE; KETONE DERIVATIVE; MAGNESIUM DERIVATIVE; REAGENT;

ARTICLE; COMPARATIVE STUDY; ENANTIOMER; ENANTIOSELECTIVITY; PROTON TRANSPORT; REACTION ANALYSIS; SYNTHESIS; TECHNIQUE;

EID: 0038237115     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2003-39291     Document Type: Article

References (19)

1. Henderson, K. W.; Kerr, W. J.; Moir, J. H. Tetrahedron 2002, 58, 4573.
2. For recent reviews, see: (a) O'Brien, P. J. Chem. Soc., Perkin Trans. 1 2001, 95. (b) O'Brien, P. J. Chem. Soc., Perkin Trans. 1 1998, 1439. (c) Simpkins, N. S. Pure Appl. Chem. 1996, 68, 691.
3. For recent reviews, see: (a) O'Brien, P. J. Chem. Soc., Perkin Trans. 1 2001, 95. (b) O'Brien, P. J. Chem. Soc., Perkin Trans. 1 1998, 1439. (c) Simpkins, N. S. Pure Appl. Chem. 1996, 68, 691.
4. For recent reviews, see: (a) O'Brien, P. J. Chem. Soc., Perkin Trans. 1 2001, 95. (b) O'Brien, P. J. Chem. Soc., Perkin Trans. 1 1998, 1439. (c) Simpkins, N. S. Pure Appl. Chem. 1996, 68, 691.
5. Henderson, K. W.; Mulvey, R. E.; Clegg, W.; O'Neil, P. A. Polyhedron 1993, 12, 2535.
6. Zhang, M.; Eaton, P. E. Angew. Chem. Int. Ed. 2002, 41, 2169.
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8. Ashby, E. C.; Willard, G. F. J. Org. Chem. 1978, 43, 4094.
9. During the preparation of this manuscript two articles have appeared detailing the use of chiral alkylmagnesium amides in enantioselective alkylation of aldehydes and in the asymmetric reduction of aryl trifluoromethylketones: (a) Yong, K. H.; Taylor, N. J.; Chong, J. M. Org. Lett. 2002, 4, 3553. (b) Yong, K. H.; Chong, J. M. Org. Lett. 2002, 4, 4139.
10. During the preparation of this manuscript two articles have appeared detailing the use of chiral alkylmagnesium amides in enantioselective alkylation of aldehydes and in the asymmetric reduction of aryl trifluoromethylketones: (a) Yong, K. H.; Taylor, N. J.; Chong, J. M. Org. Lett. 2002, 4, 3553. (b) Yong, K. H.; Chong, J. M. Org. Lett. 2002, 4, 4139.
11. Henderson, K. W.; Kerr, W. J.; Moir, J. H. Chem. Commun. 2000, 479.
12. 2.9
13. For related discussions on replacing HMPA as an additive see: (a) O'Neil, I. A.; Lai, J. Y. Q.; Wynn, D. Chem. Commun. 1999, 59. (b) Mukhopadhyay, T.; Seebach, D. Helv. Chim. Acta 1982, 65, 385.
14. For related discussions on replacing HMPA as an additive see: (a) O'Neil, I. A.; Lai, J. Y. Q.; Wynn, D. Chem. Commun. 1999, 59. (b) Mukhopadhyay, T.; Seebach, D. Helv. Chim. Acta 1982, 65, 385.
15. R = 37.97 min [(R)-6a.] }.
16. However, the reactivity of both the amide and the alkyl anions in the deprotonation reactions cannot definitively be ruled out.
17. Henderson, K. W.; Kerr, W. J.; Moir, J. H. Synlett 2001, 1253.
18. Eaton, P. E.; Lee, C. H.; Xiong, Y. J. Am. Chem. Soc. 1989, 111, 8016.
19. For a recent review of catalytic enantioselective deprotonations see: Eames, J. Eur. J. Org. Chem. 2002, 393.