Highly enantioselective synthesis of fluorinated γ-amino alcohols through proline-catalyzed cross-Mannich reaction

Organic Letters

Volumn 7, Issue 16, 2005, Pages 3433-3436

  Fustero, Santos ^a   Jiménez, Diego ^a   Sanz Cervera, Juan F ^a   Sänchez Roselló, María ^a   Esteban, Elisabet ^a   Simón Fuentes, Antonio ^a  

^a UNIVERSITY OF VALENCIA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 23944462365     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol050791f     Document Type: Article

References (53)

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44. Although proline has been recently shown to catalyze the addition of acetone to a few fluorinated aldimines, the yields obtained were generally low and the method was restricted to the use of acetone as both solvent and reagent; other ketones failed to react under these conditions. See: Funabiki, K.; Nagamori, M.; Goushi, S.; Matsui, M. Chem. Commun. 2004, 1928-1929.
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46. It is worth noting that the alternative preparation of compounds 2 through a Mannich-type addition of lithium ester enolates to trifluorom-ethylimines 1 led only to a racemic mixture of β-amino esters in moderate yield (38%) and with low diastereoselectivity (de 28%). See ref 11b.
47. Catalysts i, ii (both commercially available), and iii (Hayashi, Y.; Yamaguchi, J.; Hibino, K.; Sumiya, T.; Urushima, T.; Shoji, M.; Hashizume, D.; Koshino, H. Adv. Synth. Catal. 2004, 346, 1435-1439) failed to catalyze the cross-Mannich reaction of 1a with propanal. (Chemical Equation Presented)
48. All the new compounds that appear in Tables 1 and 2 were synthesized in racemic form as described in ref 11. For details, see Supporting Information.
49. Full details of the X-ray structure of syn-(2S,3S)-2c will be published in a full account of this work.
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51. To identify the secondary products formed, we analyzed by means of HPLC-MS methods the crude reaction mixture resulting from the condensation between aldimine 1a and 3-butenal in the same conditions as described above. The results for this analysis appear in Supporting Information.
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53. Tanaka, F.; Barbas, C. F., III. In Enantioselective Synthesis of β-Amino Acids; Juaristi, E., Soloshonok, V., Eds.; Wiley-Interscience: New York, 2005; Chapter 9, pp 195-214.