Stereoselective additions of α-lithiated alkyl-p-tolylsulfoxides to N-PMP(fluoroalkyl)aldimines. An efficient approach to enantiomerically pure fluoro amino compounds

Journal of Organic Chemistry

Volumn 62, Issue 11, 1997, Pages 3424-3425

  Bravo, Pierfrancesco ^a   Farina, Alessandra ^a   Kukhar, Valéry P ^b   Markovsky, Andrey L ^b   Meille, Stefano V ^a   Soloshonok, Vadim A ^c   Sorochinsky, Alexander E ^b   Viani, Fiorenza ^a   Zanda, Matteo ^a   Zappalà, Carmela ^a  

^a POLITECNICO DI MILANO   (Italy)

^b INSTITUTE OF BIOORGANIC CHEMISTRY AND PETROCHEMISTRY   (Ukraine)

^c NATIONAL INSTITUTE OF ADVANCED INDUSTRIAL SCIENCE AND TECHNOLOGY AIST   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

AMINE; ORGANOFLUORINE DERIVATIVE;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; IN VITRO STUDY; METHODOLOGY; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS;

EID: 8544244902     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo970004v     Document Type: Article

References (23)

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2. Bravo, P.; Zanda, M.; Zappalà, C. Tetrahedron Lett. 1996, 37, 6005.
3. (a) Filler, R.; Kobayashi, Y.; Yagupolskii, L. M. Biomedical Aspects of Fluorine Chemistry; Elsevier: Amsterdam, 1993.
4. (b) Resnati, G. Tetrahedron 1993, 49, 9385.
5. (c) Fluorine-Containing Amino Acids: Synthesis and Properties; Kukhar, V. P., Soloshonok, V. A., Eds.; Wiley: Chichester, 1994.
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10. (e) Ronan, B.; Marchalin, S.; Samuel, O.; Kagan, H. B. Tetrahedron Lett. 1989, 29, 6101.
11. (f) For a review see: Risch, N.; Arend, M. In Houben-Weyl: Methods in Organic Synthesis; Müller, E., Ed.; Thieme Verlag: Stuttgart, 1995; Vol. E21b, pp 1920-1924.
12. For recent discussions on stereochemical properties of fluorine substituents see: (a) Soloshonok, V. A.; Avilov, D. V.; Kukhar, V. P. Tetrahedron 1996, 52, 12433 and references cited therein.
13. Volkman, R. A. Additions to C-X π-bonds. In Comprehensive Organic Synthesis; Schreiber, S. L., Ed.; Pergamon Press: Oxford, 1991; Part 1, Vol. 1, Chapter 1.12.
14. Bravo, P.; Viani, F.; Zanda, M.; Fokina, N.; Kukhar, V. P.; Soloshonok, V. A.; Shishkin, O. V.; Struchkov, Y. T. Gazz. Chim. Ital. 1996, 126, 645. Attempts to use (α-fluoroalkyl)N-Cbz-aldimines as electrophiles were not satisfactory.
15. (a) Greene, T. W.; Wuts, P. G. M. Protective Groups in Organic Synthesis; Wiley: London: 1991.
16. Unfluorinated N-PMP imines were shown to exist exclusively in the anti-conformation: (b) Yamamoto, Y.; Nishii, S.; Maruyama, K.; Komatsu, T.; Ito, W. J. Am. Chem. Soc. 1986, 108, 7778.
17. Harada, K. In Chemistry of the Carbon-Nitrogen Double Bond; Patai, S., Ed.; Interscience: London, 1970; pp 69-147.
18. 19F) imines 1a-c exist as single geometrical isomers. The anti conformation was confidently assigned by analogy with the parent unfluorinated derivatives; see ref 8b.
19. 4Cl and routinely worked up. Crystallization of the crude reaction mixtures and flash chromatography of the mother liquors (hexane/ethyl acetate) afforded the desired N-PMP-FSAs 3 and 4.
20. Bravo, P.; Cavicchio, G.; Crucianelli, M.; Markovsky, L. A.; Volonterio, A.; Zanda, M. Synlett 1996, 887.
21. (a) Beck, A. K.; Seebach, D. Chem. Ber. 1991, 124, 2897.
22. 3).
23. The author has deposited atomic coordinates for 4a with the Cambridge Crystallographic Data Centre. The coordinates can be obtained, on request, from the Director, Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, CB2 1EZ, UK.