Stereoselective conjugate addition of metallated 2-methylpyridine to functionalized α,β-unsaturated carbonyl compounds

Heterocycles

Volumn 60, Issue 8, 2003, Pages 1843-1854

  Sánchez Sancho, Francisco ^a   Herradón, Bernardo ^a  

^a CSIC   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

2 CYCLOHEXENONE; BIS(2 PYRIDYLMETHYL)CYANOCUPRATE; BUTENOLIDE; CARBONYL DERIVATIVE; COPPER DERIVATIVE; ESTER; HETEROCYCLIC COMPOUND; LACTONE; LITHIUM; METAL; OXYGEN; PICOLINE; PYRIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ADDITION REACTION; ARTICLE; CHEMICAL REACTION; CONJUGATE; CRYSTAL STRUCTURE; STEREOCHEMISTRY; STRUCTURE ANALYSIS;

EID: 0041967346     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/com-03-9806     Document Type: Article

References (25)

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2. D. Lednicer, 'Strategies for Organic Drug Synthesis and Design', John Wiley and Sons, Inc., New York, 1998, pp. 242-285. D. O' Hagan, Nat. Prod. Rep., 2000, 435.
3. (a) F. Sánchez-Sancho, E. Mann, and B. Herradón, Synlett, 2000, 509.
4. (b) F. Sánchez-Sancho, E. Mann, and B. Herradón, Adv. Synth. Catal., 2001, 343, 360.
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8. O. F. Beumel Jr., W. N. Smith, and B. Rybalka, Synthesis, 1974, 43.
9. Reagent (3) has been used in the alkylation of primary halides, see: B. H. Lisphutz, D. Parker, J. A. Kozlowski, and R. D. Miller, J. Org. Chem., 1983, 48, 3334.
10. Some examples of the conjugated addition of functionalized metallated 2-methylpyridine have been reported, see: G. A. Kraus, D. R. Vines, and J. H. Malpert, Tetrahedron, 1995, 51, 1337. S. Célanire, I. Saillot-Maire, P. Ribéreau, A. Godard, and G. Quéquiner, Tetrahedron, 1999, 55, 9269.
11. Some examples of the conjugated addition of functionalized metallated 2-methylpyridine have been reported, see: G. A. Kraus, D. R. Vines, and J. H. Malpert, Tetrahedron, 1995, 51, 1337. S. Célanire, I. Saillot-Maire, P. Ribéreau, A. Godard, and G. Quéquiner, Tetrahedron, 1999, 55, 9269.
12. 3) δ 161.4 (s), 149.0 (d), 135.7 (d), 122.1 (d), 119.1 9d), 30.3 (t), -1.7 (q, 3C)]. This compound can be a useful synthetic building block (i.e.; Peterson olefination, "stable" synthetic equivalent of pyridine-2-ylmethyl anion, etc.); for related work, see: N. V. Bac and Y. Langlois, J. Am. Chem. Soc., 1982, 104, 7666. Y. Langlois, L. Konopski, N. V. Bac, A. Chiaroni, and C. Riche, Tetrahedron Lett., 1990, 31, 1865. I. P. Andrews, N. J. Lewis, A. McKillop, and A. S. Wells, Heterocycles, 1996, 43, 1151.
13. 3) δ 161.4 (s), 149.0 (d), 135.7 (d), 122.1 (d), 119.1 9d), 30.3 (t), -1.7 (q, 3C)]. This compound can be a useful synthetic building block (i.e.; Peterson olefination, "stable" synthetic equivalent of pyridine-2-ylmethyl anion, etc.); for related work, see: N. V. Bac and Y. Langlois, J. Am. Chem. Soc., 1982, 104, 7666. Y. Langlois, L. Konopski, N. V. Bac, A. Chiaroni, and C. Riche, Tetrahedron Lett., 1990, 31, 1865. I. P. Andrews, N. J. Lewis, A. McKillop, and A. S. Wells, Heterocycles, 1996, 43, 1151.
14. 3) δ 161.4 (s), 149.0 (d), 135.7 (d), 122.1 (d), 119.1 9d), 30.3 (t), -1.7 (q, 3C)]. This compound can be a useful synthetic building block (i.e.; Peterson olefination, "stable" synthetic equivalent of pyridine-2-ylmethyl anion, etc.); for related work, see: N. V. Bac and Y. Langlois, J. Am. Chem. Soc., 1982, 104, 7666. Y. Langlois, L. Konopski, N. V. Bac, A. Chiaroni, and C. Riche, Tetrahedron Lett., 1990, 31, 1865. I. P. Andrews, N. J. Lewis, A. McKillop, and A. S. Wells, Heterocycles, 1996, 43, 1151.
15. B. Herradón, Tetrahedron: Asymmetry, 1991, 2, 191.
16. F. Sánchez-Sancho, S. Valverde, and B. Herradón, Tetrahedron: Asymmetry, 1996, 7, 3209.
17. P. Permultter, 'Conjugate Addition Reactions in Organic Synthesis', Pergamon Press, Oxford, 1992.
18. We have not detected the 1,2-addition products in the reactions indicated in the equations 6, 8, and 9. Since the incompatibility of the reagent (3) and some protecting groups (from 17 and 19), we obtained a moderated yield of the conjugate addition product, highly polar compounds account for the rest of the material. On the other hand, a small amount (ca. 10%) of 1,2-addition product was obtained in the reaction of 17 with 3.
19. F. Sánchez-Sancho and B. Herradón, Tetrahedron: Asymmetry, 1998, 9, 1951.
20. B. Herradón, E. Mann, A. Salgado, and F. Sánchez-Sancho,Rec. Res. Devel. Org. Chem., 2001, 5, 49.
21. For a discussion on the like/unlike nomenclature for diastereoisomers, see: D. Seebach and V. Prelog, Angew. Chem., Int. Ed. Engl., 1982, 21, 654.
22. P. Gillespie, J. Cicariello, and G. L. Olson, Biopolymers, 1997, 43, 191. M. K. Lindvall, K. Rissanen, J. M. L. Hakala and A. M. P. Koskinen, Tetrahedron Lett., 1999, 40, 7427.
23. P. Gillespie, J. Cicariello, and G. L. Olson, Biopolymers, 1997, 43, 191. M. K. Lindvall, K. Rissanen, J. M. L. Hakala and A. M. P. Koskinen, Tetrahedron Lett., 1999, 40, 7427.
24. The MD simulations were carried out in the vacuum using Amber 94 force field. We thank Mercedes Alonso (IQOG, CSIC) for performing the calculations.
25. 2; R indices: R1 [I > 2σ] = 0.0650; R indices (all data): wR2 = 0.1670.