Transition metal-catalyzed diastereoselective aldol reactions of prochiral ketones with methyl isocyanoacetate

Tetrahedron Letters

Volumn 37, Issue 43, 1996, Pages 7845-7848

  Soloshonok, Vadim A ^a,c   Kacharov, Alexey D ^a   Avilov, Dimitry V ^a   Hayashi, Tamio ^b  

^a INSTITUTE OF BIOORGANIC CHEMISTRY AND PETROCHEMISTRY   (Ukraine)

^b KYOTO UNIVERSITY   (Japan)

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

Author keywords

[No Author keywords available]

Indexed keywords

OXAZOLINE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030597177     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01746-7     Document Type: Article

References (9)

1. 2 Peptide Chemistry: Design and Synthesis of Peptides, Conformational Analysis and Biological Functions; Hruby V. J.; Schwyzer, R., Eds.; Tetrahedron-Symposia-in-Print, 31; Tetrahedron 1988, 44, 661.
2. 3 For recent comprehensive reviews on asymmetric synthesis of α-amino acids see: (a) Williams, R. Synthesis of Optically Active α-Amino Acids; Pergamon Press: Oxford, 1989; and
3. (b) Duthaler, R. P. Tetrahedron 1994, 50, 1539.
4. 4 Soloshonok, V. A.; Hayashi, T.; Ishikawa, K.; Nagashima, N. Tetrahedron Lett. 1994, 35, 1055.
5. 5 For recent stereoselective approaches to this class of amino acids see: (a) Soloshonok, V. A.; Kukhar', V. P.; Galushko, S. V.; Svistunova, N. Yu.; Avilov, D. V.; Kuz'mina, N. A.; Raevski, N. I.; Struchkov, Yu. T.; Pysarevsky A. P.; Belokon' Yu. N. J. Chem. Soc., Perkin Trans. 1 1993, 3143.
6. (b) Sting, A. R,; Seebach, D. Tetrahedron 1996, 52, 279.
7. (c) Soloshonok, V. A.; Avilov, D. V.; Kukhar', V. P. Tetrahedron: Asymmetry 1996, 7, 1547.
8. 6 Relative trans-configuration of oxazoline 3k was confirmed via its acidic hydrolysis to the corresponding amino acid, (2R*,3R*)-configuration of which was established by comparison with the sample of known absolute stereochemistry; see ref. 5. Similarly, trans-configuration of 3l,m was confirmed. To the rest of oxazolines 3f-j,n-p trans-configuration was assigned on the basis of an apparent similarity of their NMR spectra to the patterns of 3k-m; see ref. 7. In the case of hydrocarbon derivatives 3q,r, relative configuration of the dominant diastereomer has not been established, but is assumed to be trans on the basis of similarity of their NMR spectra to the patterns of 3f-p, and stereochemical preferences revealed for these reactions.
9. AB = 11.9 Hz, 2 H), 3.79 (s, 3 H), 4.50 (d, J = 2.0 Hz, 1 H), 6.97 (d, J = 2.0 Hz, 1 H). 3i: 1.56 (s, 3 H), 3.81 (s, 3 H), 4.91 (m, 1 H), 5.73 (d, J = 0.66 Hz, 1 H), 6.98 (d, J = 1.3 Hz, 1 H). 4i: 1.76 (s, 3 H), 3.80 (s, 3 H), 4.56 (m, 1 H), 6.20 (s, 1 H), one resonance is obscured. 3j: 1.75 (s, 3 H), 3.83 (s, 3 H), 5.07 (d, J = 2.0 Hz, 1 H), 7.04 (d, J = 2.0 Hz, 1 H). 3k: 1.51 (s, 3 H), 3.82 (s, 3 H), 4.90 (d, J = 2.0 Hz, 1 H), 6.98 (d, J = 2.0 Hz, 1 H). 3l: 0.84-0.89 (m, 3 H), 1.24-1.41 (m, 10 H), 1.82-2.05 (m, 2 H), 3.81 (s, 3 H), 4.90 (d, J = 2.0 Hz, 1 H), 6.98 (d, J = 2.0 Hz, 1 H). 3m: 0.85-0.90 (m, 3 H), 1.25-1.41 (m, 12 H), 1.82-1.98 (m, 2 H), 3.82 (s, 3 H), 4.91 (d, J = 2.3 Hz, 1 H), 6.99 (d, J = 2.3 Hz, 1 H). 4n: 0.93-2.20 (m, 11 H), 3.78 (s, 3 H), 4.78 (d, J = 2.0 Hz, 1 H), 6.97 (d, J = 2.3 Hz, 1 H). 3o: 3.81 (s, 3 H), 5.10 (d, J = 2.1 Hz, 1 H), 7.08 (d, J = 2.1 Hz, 1 H), 7.26-7.48 (m, 5 H), 3p: 0.81-0.88 (m, 3 H), 1.22-1.40 (m, 8 H), 1.83-2.07 (m, 2 H), 3.81 (s, 3 H), 4.99 (d, J = 2.0 Hz, 1 H), 7.07 (d, J = 2.0 Hz, 1 H). 3q: 0.97 (t, J = 7.6 Hz, 3 H), 1.27 (s, 3 H), 1.79 (q.d, J = 7.6 Hz, J = 1.8 Hz, 2H), 3.76 (s, 3 H), 4.42 (d, J = 2.0 Hz, 1 H), 6.92 (m, 1 H). 4q: 0.94 (t, J = 7.6 Hz, 3 H), 1.48 (s, 3 H), 1.65 (m, 2H), 3.75 (s, 3 H), 4.40 (d, J = 2.2 Hz, 1 H), one resonance is obscured. 3r: 0.95-1.97 (m, 11 H), 1.24 (s, 3 H), 3.76 (s, 3 H), 4.52 (d, J = 2.0 Hz, 1 H), 6.92 (d, J = 2.0 Hz, 1 H).