Asymmetric aldol reactions of trifluoromethyl ketones with a chiral Ni(II) complex of glycine: Stereocontrolling effect of the trifluoromethyl group

Tetrahedron

Volumn 52, Issue 38, 1996, Pages 12433-12442

  Soloshonok, Vadim A ^a   Avilov, Dimitry V ^b   Kukhar, Valery P ^b  

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

^b INSTITUTE OF BIOORGANIC CHEMISTRY AND PETROCHEMISTRY   (Ukraine)

Author keywords

[No Author keywords available]

Indexed keywords

ORGANOFLUORINE DERIVATIVE; SERINE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY; TECHNIQUE;

EID: 0030590464     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4020(96)00741-7     Document Type: Article

References (49)

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43. 15 (2S,3S) Configuration, a consequence of the Cahn-Ingold-Prelog priority, is stereochemically equivalent to the (2S,3R) configuration in the hydrocarbon analogs; Cahn, R.S.; Ingold, C.; Prelog, V. Angew. Chem. Int. Ed. Engl. 1966, 5, 385.
44. 2"; Smart, B.S. in Organofluorine Chemistry: Principles and Commercial Applications, eds. Banks, R.E.; Smart, B.E.; Tatlow, J.C., Plenum Press, New York, 1994, pp. 57-88.
45. 17 Formation of the stabilized hydroxyl-co-ordinated intermediates is also supported by the observation that the reactions under study as well as the high diastereoselectivity could be observed only under the conditions (NaOMe/MeOH, MeCN/DBU) which provide ionization of the hydroxyl group on the side chain of the resultant aldol products.
46. 19
47. 19(a) Soloshonok, V.A.; Hayashi, T.; Ishikawa, K.; Nagashima, N. Tetrahedron Lett. 1994, 55, 1055.
48. (b) Soloshonok, V.A.; Kacharov, A.D.; Avilov, D.V.; Hayashi, T. submitted for publication.
49. 20 Edwards, F.N. in Organofluorine Chemistry: Principles and Commercial Applications, eds. Banks, R.E.; Smart, B.E.; Tatlow, J.C., Plenum Press, New York, 1994, pp. 501-541; see also ref. 16.