Stereoselective synthesis of α-silylamines by the direct addition of silyl anions to activated imines

Organic Letters

Volumn 7, Issue 7, 2005, Pages 1403-1406

  Ballweg, David M ^a   Miller, Rebecca C ^a   Gray, Danielle L ^a   Scheidt, Karl A ^a  

^a NORTHWESTERN UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINE; ANION; CARBON; IMINE; SILANE DERIVATIVE;

ADDITION REACTION; ARTICLE; STEREOCHEMISTRY; SYNTHESIS;

EID: 17444405334     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol050244u     Document Type: Article

References (45)

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23. Preliminary data suggests that reductive coupling products are the predominant species from these reactions. This intriguing possibility is currently under investigation.
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26. Fewer equivalents of silyl anion result in lower isolated yields.
27. A Representative Proceedure. To a 25 mL Schlenk flask was added 1 equiv of imine and THF (0.2 M), and the mixture was cooled to -78°C. To this solution was added 3 equiv of silyllithium (approximately 1 M in THF). After being stirred at -78°C for 20 min, the reaction was quenched with 5% acetic acid in methanol (10 mL) at -78°C. The mixture was diluted with ethyl acetate and then washed with water and brine. After drying, the remaining residue was purified using flash chromatography to yield pure protected α-silylamines.
28. The structures of these unusual compounds have been confirmed by X-ray crystallography. See the Supporting Information for details.
29. The use of nitro aromatic imines afforded no products, presumably due to complications resulting from incompatibilities with the silyl anion.
30. The acetophenone-derived imine afforded only 11% yield of desired product (42% recovered imine). Studies to attenuate of the basicity of the silyl anions to successfully engage this class of imine are currently underway.
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32. For selected examples of transformations of arylsilanes, see: (a) Bonini, B. F.; Comes-Franchini, M.; Fochi, M.; Laboroi, F.; Mazzanti, G.; Ricci, A.; Varchi, G. J. Org. Chem. 1999, 64, 8008-8013. (b) Denmark, S. E.; Sweis, R. F. Chem. Pharm. Bull. 2002, 50, 1531-1541. (c) Ichikawa, J.; Ishibashi, Y.; Fukui, H. Tetrahedron Lett. 2003, 44, 707-710.
33. For selected examples of transformations of arylsilanes, see: (a) Bonini, B. F.; Comes-Franchini, M.; Fochi, M.; Laboroi, F.; Mazzanti, G.; Ricci, A.; Varchi, G. J. Org. Chem. 1999, 64, 8008-8013. (b) Denmark, S. E.; Sweis, R. F. Chem. Pharm. Bull. 2002, 50, 1531-1541. (c) Ichikawa, J.; Ishibashi, Y.; Fukui, H. Tetrahedron Lett. 2003, 44, 707-710.
34. Corey, E. J.; Lee, T. W. Org. Lett. 2001, 3, 3337-3339 and references therein.
35. For reviews of sultinyl imines in synthesis, see: (a) Zhou, P.; Chen, B.-C.; Davis, F. A. Tetrahedron 2004, 60, 8003-8030. (b) Davis, F. A.; Zhou, P.; Chen, B. C. Chem. Soc. Rev. 1998, 27, 13-18. (c) Ellman, J. A.; Owens, T. D.; Tang, T. P. Acc. Chem. Res. 2002, 35, 984-995.
36. For reviews of sultinyl imines in synthesis, see: (a) Zhou, P.; Chen, B.-C.; Davis, F. A. Tetrahedron 2004, 60, 8003-8030. (b) Davis, F. A.; Zhou, P.; Chen, B. C. Chem. Soc. Rev. 1998, 27, 13-18. (c) Ellman, J. A.; Owens, T. D.; Tang, T. P. Acc. Chem. Res. 2002, 35, 984-995.
37. For reviews of sultinyl imines in synthesis, see: (a) Zhou, P.; Chen, B.-C.; Davis, F. A. Tetrahedron 2004, 60, 8003-8030. (b) Davis, F. A.; Zhou, P.; Chen, B. C. Chem. Soc. Rev. 1998, 27, 13-18. (c) Ellman, J. A.; Owens, T. D.; Tang, T. P. Acc. Chem. Res. 2002, 35, 984-995.
38. For a related approach utilizing trialkylstannane nucleophiles, see: Kells, K. W.; Chong, J. M. Org. Lett. 2003, 5, 4215-4218.
39. Information regarding the X-ray analysis of 31 is as follows: crystal system: orthorhombic, space group P212121, unit cell dimensions 6.4 × 16.6 × 18.3 Å. Data were collected on a Bruker Smart 1000 CCD with Mo Kα radiation. CCDC 257698 (ent-25), CCDC 257699 (31), and CCDC 257700 (11) contain the supplementary crystallographic data for these structures. These data can be obtained online free of charge (or from the Cambridge Crystallographic Data Centre, 12, Union Road, Cambridge CB2 1EZ, U.K.; fax (+44) 1223-336-033; deposit@cdc.cam.ac.uk). For an X-ray structure of a related α-silylamine, see: Bolm, C.; Kasyan, A.; Drauz, K.; Gunther, K.; Raabe, G. Angew. Chem., Int. Ed. 2000, 39, 2288-2290.
40. For an example of Si-O interactions in the solid state, see: Dixon, D. A.; Hertler, W. R.; Chase, D. B.; Farnham, W. B.; Davidson, F. Inorg. Chem. 1988, 27, 4012-4018 and references therein. For a review of hypervalent silicon, see: Chuit, C.; Corriu, R. J. P.; Reye, C.; Young, J. C. Chem. Rev. 1993, 93, 1371-1448.
41. For an example of Si-O interactions in the solid state, see: Dixon, D. A.; Hertler, W. R.; Chase, D. B.; Farnham, W. B.; Davidson, F. Inorg. Chem. 1988, 27, 4012-4018 and references therein. For a review of hypervalent silicon, see: Chuit, C.; Corriu, R. J. P.; Reye, C.; Young, J. C. Chem. Rev. 1993, 93, 1371-1448.
42. Liu, G. C.; Cogan, D. A.; Ellman, J. A. J. Am. Chem. Soc. 1997, 119, 9913-9914.
43. The X-ray crystallographic structure of ent-25 also displays a high preference for this unusual diastereomeric pattern. In contrast, the opposite diastereoselectivity is observed with seemingly related tralkylstannyl anion additions, see ref 19.
44. (a) Cogan, D. A.; Liu, G. C.; Ellman, J. Tetrahedron 1999, 55, 8883-8904.
45. (b) For an example of diastereoselective phosphite additions to enantiopure sulfinylimines, see: Lefebvre, I. M.; Evans, S. A., Jr. J. Org. Chem. 1997, 62, 7532-7533.