Diastereoselective reaction of [1-(2,4,6-triisopropylphenylsulfinyl)-2-naphthyl]methanimines via diastereomeric rotamers

Author:

Nakamura Shuichi,Yasuda Hiroki,Toru Takeshi

Publisher

Elsevier BV

Subject

Inorganic Chemistry,Organic Chemistry,Physical and Theoretical Chemistry,Catalysis

Reference28 articles.

1. For the reaction of (o-tert-butylphenyl)maleimide, see: (a) Kishikawa, K.; Tsuru, I.; Kohmoto, S.; Yamamoto, M.; Yamada, K. Chem. Lett. 1994, 1605–1606; (b) Curran, D. P.; Qi, H.; Geib, S. J.; DeMello, N. C. J. Am. Chem. Soc. 1994, 116, 3131–3132; (c) Curran, D. P.; Geib, S.; DeMello, N. Tetrahedron 1999, 55, 5681–5704.

2. For the reaction of N-acyl-o-tert-butylanilides, see: (a) Hughes, A. D.; Price, D. A.; Shishkin, O.; Simpkins, N. S. Tetrahedron Lett. 1996, 37, 7607–7610; (b) Kitagawa, O.; Izawa, H.; Taguchi, T.; Shiro, M. Tetrahedron Lett. 1997, 38, 4447–4450; (c) Kitagawa, O.; Izawa, H.; Sato, K.; Dobashi, A.; Taguchi, T.; Shiro, M. J. Org. Chem. 1998, 63, 2634–2640; (d) Hughes, A. D.; Simpkins, N. S. Synlett 1998, 967–968; (e) Hughes, A. D.; Price, D. A.; Simpkins, N. S. J. Chem. Soc., Perkin Trans. 1 1999, 1295–1304; (f) Fujita, M.; Kitagawa, O.; Izawa, H.; Dobashi, A.; Fukaya, H.; Taguchi, T. Tetrahedron Lett. 1999, 40, 1949–1952; (g) Kitagawa, O.; Momose, S.; Fushimi, Y.; Taguchi, T. Tetrahedron Lett. 1999, 40, 8827–8831; (h) Bach, T.; Schröder, J.; Harms, K. Tetrahedron Lett. 1999, 40, 9003–9004; (i) Curran, D. P.; Liu, W.; Chen, C. H. J. Am. Chem. Soc. 1999, 121, 11012–11013; (j) Fujita, M.; Kitagawa, O.; Yamada, Y.; Izawa, H.; Hasegawa, H; Taguchi, T. J. Org. Chem. 2000, 65, 1108–1114; (k) Kitagawa, O.; Fujita, M.; Kohriyama, M.; Hasegawa, H.; Taguchi, T. Tetrahedron Lett. 2000, 41, 8539–8544.

3. For the reaction of N,N-diisopropylnaphthamide, see: (a) Clayden, J.; Westlund, N.; Wilson, F. X.; Tetrahedron Lett. 1996, 37, 5577–5580; (b) Clayden, J. Angew. Chem., Int. Ed. Engl. 1997, 36, 949–951; (c) Clayden, J.; Westlund, N.; Wilson, F. X. Tetrahedron Lett. 1999, 40, 3329–3330; (d) Bragg, R. A.; Clayden, J. Tetrahedron Lett. 1999, 40, 8323–8326; (e) Bragg, R. A.; Clayden, J. Tetrahedron Lett. 1999, 40, 8327–8331; (f) Clayden, J.; Westlund, N.; Wilson, F. X. Tetrahedron Lett. 1999, 40, 7883–7887; (g) Clayden, J.; Westlund, N.; Beddoes, R. L.; Helliwell, M. J. Chem. Soc., Perkin Trans. 1 2000, 1351–1361; (h) Clayden, J.; McCarthy, C.; Westlund, N.; Frampton, C. S. J. Chem. Soc., Perkin Trans. 1 2000, 1363–1378; (i) Clayden, J.; Westlund, N.; Frampton, C. S. J. Chem. Soc., Perkin Trans. 1 2000, 1379–1385; (j) Clayden, J.; McCarthy, C.; Cumming, J. G. Tetrahedron Lett. 2000, 41, 3279–3283; (k) Clayden, J.; Helliwell, M.; McCarthy, C.; Westlund, N. J. Chem. Soc., Perkin Trans. 1 2000, 3232–3249; (l) Clayden, J.; Johnson, P.; Pink, J. H.; Helliwell, M. J. Org. Chem. 2000, 65, 7033–7040; (m) Dai, W.; Lau, C. W. Tetrahedron Lett. 2001, 42, 2541–2544.

4. Asymmetric deprotonation of N,N-dihexyl-1-naphthamides to provide atropisomers of N,N-dihexyl-2-alkyl-1-naphthamides

5. Enantiomeric resolution by HPLC of axial chiral amides using amylose tris[(S)-1-phenylethylcarbamate]

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