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Volumn 68, Issue 8, 2003, Pages 3241-3245

Orthoacylimines: A new class of chiral auxiliaries for nucleophilic addition of organolithium reagents to imines

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL REAGENTS; CHIRAL COMPOUNDS;

EID: 0037453686     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo026571m     Document Type: Article
Times cited : (26)

References (41)
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    • (a) Higashiyama, K.; Inoue, H.; Takahashi, H. Tetrahedron Lett. 1992, 33, 235-238. (b) Higashiyama, K.; Inoue, H.; Takahashi, H. Tetrahedron 1994, 50, 1083-1092. (c) Davis, F. A.; Zhang, Y.; Andemichael, Y.; Fang, T.; Fanelli, D. L.; Zhang, H. J. Org. Chem. 1999, 64, 1403-1406. (d) Liu, G.; Cogan, D. A.; Ellman, J. A. J. Am. Chem. Soc. 1997, 119, 9913-9914. (e) Yang, T. K.; Chen, R. Y.; Lee, D. S.; Peng, W. S.; Jiang, Y. Z.; Mi, A. Q.; Jong, T. T. J. Org. Chem. 1994, 59, 914-921. For a recent report on an improved and practical auxiliary, see: (f) Han, Z.; Krishnamurthy, D.; Grover, P.; Fang, K.; Senanayake, C. H. J. Am. Chem. Soc. 2002, 124, 7880-7881.
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    • note
    • Although we could directly submit the crude imine to the nucleophilic addition conditions, only decomposition occurred upon treatment with alkyllithium reagents. This is presumably due to the competitive enolization reaction of the alkylimine.
  • 38
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    • note
    • Additives such as DMPU, TMEDA, and HMPA were also tested, but no increase in the diastereocontrol could be observed. The addition of Lewis acids was also not effective in improving the selectivities.


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