Stereoselective addition reactions to chiral N-benzylidene-P-toluenesulfinamides. Application to the synthesis of optically active 1,2-diphenylethylamines

Tetrahedron Asymmetry

Volumn 8, Issue 4, 1997, Pages 591-598

  Moreau, Pascale ^a   Essiz, Munir ^a   Mérour, Jean Yves ^b   Bouzard, Daniel ^a  

^a BRISTOL MYERS SQUIBB   (United States)

^b UNIVERSITÉ D'ORLÉANS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

BENZALDEHYDE DERIVATIVE; PHENETHYLAMINE DERIVATIVE;

ARTICLE; CHIRALITY; CRYSTALLIZATION; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0031579418     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(96)00541-1     Document Type: Article

References (11)

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2. 2. a) Eddine, J.J.; Cherqaoui, M. Tetrahedron Asymm. 1995, 6, 1225-1228.
3. b) Natsuka, K.; Nakamura, H.; Uno, H.; Umemoto, S. J. Med. Chem. 1975, 18, 1240-1244.
4. c) Andreoli, P.; Billi, L.; Cainelli, G.; Panunzio, M.; Martelli, G.; Spunta, G. J. Org. Chem. 1990, 55, 4199-4200.
5. 3. Denmark, S.E.; Nicaise, O. Synlett 1993, 359-361.
6. 4. Wu, M.-J.; Pridgen, L.N. J. Org. Chem. 1991, 56, 1340-1344.
7. 5. Davis, FA.; Reddy, R.E.; Szewczyk, J.M. J. Org. Chem. 1995, 60, 7037-7039.
8. 6. Davis, FA.; Reddy, R.E.; Szewczyk, J.M.; Portonovo, P.S. Tetrahedron Lett. 1993, 34, 6229-6232.
9. 7. All the starting aromatic aldehydes were obtained from commercial suppliers and used without further purification except for compound 1f, which was prepared in 97% yield by treatment of o-salicylaldehyde with 1.1 equiv. of NaH and 1.5 equiv. of benzyl bromide in THF at room temperature.
10. 8. Hua, D.H.; Miao, S.W.; Chen, J.S.; Iguchi, S. J. Org. Chem. 1991, 56, 4-6.
11. 9. Hulce, M.; Mallamo, J.P.; Frye, L.L.; Kogan, T.P.; Posner, G.H. Org. Synth. 1984, 64, 196-206.