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Volumn 125, Issue 33, 2003, Pages 9900-9901

Catalytic asymmetric cyanosilylation of ketones with chiral Lewis base

Author keywords

[No Author keywords available]

Indexed keywords

BASE; KETONE DERIVATIVE;

EID: 0042522434     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja036222p     Document Type: Article
Times cited : (247)

References (47)
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    • For other recent examples of catalytic enantioselective nucleophilic addition to ketones, see: (a) Evans, D. A.; Burgey, C. S.; Kozlowsky, M. C.; Tregay, S. W. J. Am. Chem. Soc. 1999, 121, 686. (b) Evans, D. A.; Johnson, J. Acc. Chem. Res. 2000, 33, 325. (c) Denmark, S. E.; Fan, Y. J. Am. Chem. Soc. 2002, 124, 4233. (d) Waltz, K. M.; Gavenonis, J.; Walsh, P. J. Angew. Chem, Int. Ed. 2002, 41, 3697. (e) Garcia, C.; LaRochelle, L. K.; Walsh, P. J. J. Am. Chem. Soc. 2002, 124, 10970. (f) DiMauro, E. F.; Kozlowski, M. C. J. Am. Chem. Soc. 2002, 124, 12666. (g) DiMauro, E. F.; Kozlowski, M. C. Org. Lett. 2002, 4, 3781.
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    • For other recent examples of catalytic enantioselective nucleophilic addition to ketones, see: (a) Evans, D. A.; Burgey, C. S.; Kozlowsky, M. C.; Tregay, S. W. J. Am. Chem. Soc. 1999, 121, 686. (b) Evans, D. A.; Johnson, J. Acc. Chem. Res. 2000, 33, 325. (c) Denmark, S. E.; Fan, Y. J. Am. Chem. Soc. 2002, 124, 4233. (d) Waltz, K. M.; Gavenonis, J.; Walsh, P. J. Angew. Chem, Int. Ed. 2002, 41, 3697. (e) Garcia, C.; LaRochelle, L. K.; Walsh, P. J. J. Am. Chem. Soc. 2002, 124, 10970. (f) DiMauro, E. F.; Kozlowski, M. C. J. Am. Chem. Soc. 2002, 124, 12666. (g) DiMauro, E. F.; Kozlowski, M. C. Org. Lett. 2002, 4, 3781.
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    • For other recent examples of catalytic enantioselective nucleophilic addition to ketones, see: (a) Evans, D. A.; Burgey, C. S.; Kozlowsky, M. C.; Tregay, S. W. J. Am. Chem. Soc. 1999, 121, 686. (b) Evans, D. A.; Johnson, J. Acc. Chem. Res. 2000, 33, 325. (c) Denmark, S. E.; Fan, Y. J. Am. Chem. Soc. 2002, 124, 4233. (d) Waltz, K. M.; Gavenonis, J.; Walsh, P. J. Angew. Chem, Int. Ed. 2002, 41, 3697. (e) Garcia, C.; LaRochelle, L. K.; Walsh, P. J. J. Am. Chem. Soc. 2002, 124, 10970. (f) DiMauro, E. F.; Kozlowski, M. C. J. Am. Chem. Soc. 2002, 124, 12666. (g) DiMauro, E. F.; Kozlowski, M. C. Org. Lett. 2002, 4, 3781.
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    • Waltz, K.M.1    Gavenonis, J.2    Walsh, P.J.3
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    • For other recent examples of catalytic enantioselective nucleophilic addition to ketones, see: (a) Evans, D. A.; Burgey, C. S.; Kozlowsky, M. C.; Tregay, S. W. J. Am. Chem. Soc. 1999, 121, 686. (b) Evans, D. A.; Johnson, J. Acc. Chem. Res. 2000, 33, 325. (c) Denmark, S. E.; Fan, Y. J. Am. Chem. Soc. 2002, 124, 4233. (d) Waltz, K. M.; Gavenonis, J.; Walsh, P. J. Angew. Chem, Int. Ed. 2002, 41, 3697. (e) Garcia, C.; LaRochelle, L. K.; Walsh, P. J. J. Am. Chem. Soc. 2002, 124, 10970. (f) DiMauro, E. F.; Kozlowski, M. C. J. Am. Chem. Soc. 2002, 124, 12666. (g) DiMauro, E. F.; Kozlowski, M. C. Org. Lett. 2002, 4, 3781.
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    • Garcia, C.1    LaRochelle, L.K.2    Walsh, P.J.3
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    • 0037202209 scopus 로고    scopus 로고
    • For other recent examples of catalytic enantioselective nucleophilic addition to ketones, see: (a) Evans, D. A.; Burgey, C. S.; Kozlowsky, M. C.; Tregay, S. W. J. Am. Chem. Soc. 1999, 121, 686. (b) Evans, D. A.; Johnson, J. Acc. Chem. Res. 2000, 33, 325. (c) Denmark, S. E.; Fan, Y. J. Am. Chem. Soc. 2002, 124, 4233. (d) Waltz, K. M.; Gavenonis, J.; Walsh, P. J. Angew. Chem, Int. Ed. 2002, 41, 3697. (e) Garcia, C.; LaRochelle, L. K.; Walsh, P. J. J. Am. Chem. Soc. 2002, 124, 10970. (f) DiMauro, E. F.; Kozlowski, M. C. J. Am. Chem. Soc. 2002, 124, 12666. (g) DiMauro, E. F.; Kozlowski, M. C. Org. Lett. 2002, 4, 3781.
    • (2002) J. Am. Chem. Soc. , vol.124 , pp. 12666
    • DiMauro, E.F.1    Kozlowski, M.C.2
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    • 0013130960 scopus 로고    scopus 로고
    • For other recent examples of catalytic enantioselective nucleophilic addition to ketones, see: (a) Evans, D. A.; Burgey, C. S.; Kozlowsky, M. C.; Tregay, S. W. J. Am. Chem. Soc. 1999, 121, 686. (b) Evans, D. A.; Johnson, J. Acc. Chem. Res. 2000, 33, 325. (c) Denmark, S. E.; Fan, Y. J. Am. Chem. Soc. 2002, 124, 4233. (d) Waltz, K. M.; Gavenonis, J.; Walsh, P. J. Angew. Chem, Int. Ed. 2002, 41, 3697. (e) Garcia, C.; LaRochelle, L. K.; Walsh, P. J. J. Am. Chem. Soc. 2002, 124, 10970. (f) DiMauro, E. F.; Kozlowski, M. C. J. Am. Chem. Soc. 2002, 124, 12666. (g) DiMauro, E. F.; Kozlowski, M. C. Org. Lett. 2002, 4, 3781.
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    • DiMauro, E.F.1    Kozlowski, M.C.2
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    • note
    • For the structures of the commercially available modified cinchona alkaloids, see the Supporting Information.
  • 27
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    • For recent reviews, see: (a) Yoon, T. P.; Jacobsen, E. N. Science 2003, 299, 1691-1693.
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    • Yoon, T.P.1    Jacobsen, E.N.2
  • 45
    • 0042180844 scopus 로고    scopus 로고
    • note
    • As described in the Supporting Information, a wide variety of α,α-dialkoxy ketones (6a-c, 7a-m) can be prepared from commercially available reagents such as α,α-dialkoxyacetonitrile, arylglyoxal monohydrate, and 1,3-dihydroxyacetone dimer in one or two steps.
  • 46
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    • note
    • Simple ketones afford generally modest enantioselectivity (10-76% ee).
  • 47
    • 0041680151 scopus 로고    scopus 로고
    • note
    • For experimental details, see the Supporting Information.


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