Facile synthesis of optically pure 1,2-diaryl (and 1-alkyl-2-aryl) ethyl and propylamines

Organic Letters

Volumn 5, Issue 5, 2003, Pages 677-680

  García Ruano, José L ^a   Alemán, José ^a   Soriano, José F ^a  

^a UNIVERSIDAD AUTÓNOMA DE MADRID   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

CARBON; ETHYLAMINE; LITHIUM; NITROGEN; PROPYLAMINE; TOLUENESULFONAMIDE DERIVATIVE;

ADDITION REACTION; ARTICLE; CRYSTALLIZATION; ENANTIOMER; PROTON NUCLEAR MAGNETIC RESONANCE; PURIFICATION; QUANTUM YIELD; STEREOCHEMISTRY; SUBSTITUTION REACTION; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

EID: 0141629828     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol027464h     Document Type: Article

References (44)

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19. However, N-t-butanesulfinylimines with alkoxy groups at C-α afforded poorer stereoselectivity in the attack of benzylic anions (0-55% de); see: Barrow, J. C.; Ngo, P. L.; Pellicore, J. M.; Selnick, H. G.; Nantermet, P. G. Tetrahedron Lett. 2001, 42, 2051.
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22. In this work, the use of the sterically more demanding N-naphalenesulfinyl arylimine was required to increase the de up to 96%. See: Davis, F. A.; Pradyudmna, K. M. J. Org. Chem. 2002, 67, 1290.
23. Recent references: (a) Cutter, P. S.; Miller, R. B.; Schore, N. E. Tetrahedron 2002, 58, 1471. (b) Laumer, J. M.; Kim, D. D.; Beak, P. J. Org. Chem. 2002, 67, 6797. (c) Katritzky, A. R.; Suzuki, K.; He, H.-Y. J. Org. Chem. 2002, 67, 8224.
24. Recent references: (a) Cutter, P. S.; Miller, R. B.; Schore, N. E. Tetrahedron 2002, 58, 1471. (b) Laumer, J. M.; Kim, D. D.; Beak, P. J. Org. Chem. 2002, 67, 6797. (c) Katritzky, A. R.; Suzuki, K.; He, H.-Y. J. Org. Chem. 2002, 67, 8224.
25. Recent references: (a) Cutter, P. S.; Miller, R. B.; Schore, N. E. Tetrahedron 2002, 58, 1471. (b) Laumer, J. M.; Kim, D. D.; Beak, P. J. Org. Chem. 2002, 67, 6797. (c) Katritzky, A. R.; Suzuki, K.; He, H.-Y. J. Org. Chem. 2002, 67, 8224.
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27. Moderate configurational stability of benzyl sulfoxides due to the sulfoxide-sulfenate rearrangement and, mainly, low thermal stability of the amines resulting from their reactions with N-sulfinylimines, prone to desulfinylation, should be expected.
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31. This allowed for the rapid preparation of these compounds on a multigram scale, with no chromatographic separation being needed.
32. See Supporting Information for experimental details concerning the synthesis of this compound.
33. From the results obtained in reactions of 4 with other achiral N-aryl aldimines, we have checked that the level of the asymmetric induction depends on the group joined to the iminic nitrogen. De values become higher than those achieved by benzylation of N-sulfinylimines in ref 5. These results will be published in due course.
34. Reactions of 2 and 4 with (S)-1a could be successfully performed on a gram scale (see Supporting Information for experimental details).
35. The (R) or (S) stereochemical notation assigned to C(1) in compounds 3 and 5-9 depends on the nature of the R group.
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37. Reactions of compound 4 required 30-40 min for completion, whereas less than 20 min were required for the reactions of compound 2.
38. Stereochemistry for 5′e has not been unequivocally established.
39. Atomic coordinates for 5h, 5i, and 3i have been deposited with the Cambridge Crystallographic Data Centre (deposition numbers CCDC 197 388, 197 389, and 197 390, respectively). The coordinates can be obtained, upon request, from the Director, Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge Cb2 1EZ, UK.
40. Berova, N. D.; Kurtev, B. J. Tetrahedron 1969, 25, 2301.
41. Favored conformations around the N-S bond in these approaches are those displaying the lone electron pair at sulfur oriented towards the anion, thus minimizing the interactions between both SOTol groups.
42. As approach will be relatively destabilized in the case of the reaction of 4 with 1e because of the orientation of the naphthalene ring, which would strongly interact with the methyl group at benzyl carbanion. This would explain the lower de observed in the entry 5 of Table 3.
43. Lower yields of some unidentified amine derivatives are obtained by using EtOH as the solvent.
44. De values higher than 98% were determined for 8f and 9f by using the Mösher amides protocol. The same conclusion could be deduced for 8a and 9a from their specific rotations (see Supporting Information).