Stereoselective Stobbe condensation of ethyl methyl diphenylmethylenesuccinate with aromatic aldehydes

Organic Letters

Volumn 4, Issue 20, 2002, Pages 3521-3524

  Liu, Jin ^a   Brooks, Neil R ^b  

^a MURRAY STATE UNIVERSITY   (United States)

^b University of Minnesota   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ARTICLE;

EID: 0042703896     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol026668v     Document Type: Article

References (16)

1. Liu, J.; Liu, R. S. H.; Simmons, C. J. Tetrahedron Lett. 1997, 38, 3999-4002.
2. Johnson, W. S.; Daub, G. H. In Organic Reactions, Vol. 6; John Wiley and Sons: New York, 1951; pp 2-73.
3. Yokoyama, Y. Chem. Rev. 2000, 100, 1717-1739.
4. Heller, H.; Ottaway, M. J. J. Chem. Soc., Chem. Commun. 1995, 479-480.
5. Janicki, S. Z.; Schuster, G. B. J. Am. Chem. Soc. 1995, 117, 8524-8527.
6. Hart, R. J.; Heller, H. G. J. Chem. Soc., Perkin Trans. 1 1972, 1321-1324.
7. 4.
8. 3) at 173(2) K using a Bruker SMART area diffractometer, λ (Mo Ka) = 0.71073 Å. Data integration was carried out with SAINT V6.1 (Bruker Analytical X-ray Systems, Madison, WI), corrections for absorption and decay were applied using SADABS. The structure was solved, by direct methods, and refined using the SHELXTL-Plus V5.10. All non-hydrogen atoms were refined with anisotropic thermal parameters. Hydrogen atoms were placed with ideal positions and refined with isotropic thermal parameters related to the parent carbon atom. R1 = 0.0367 for 2732 data [I>2_(I)] and = 0.0418 for all 3093 data.
9. Selected bond lengths: C(3)-C(4) = 1.4671(17); C(3)-C(6) = 1.3519(18); C(4)-C(7) = 1.3751(18); C(6)-C(8) = 1.4586(18); C(7)-C(14) = 1.4803(17); C(7)-C(20) = 1.4808(17) Å. Selected bond angles: C(6)-C(3)-C(4) = 137.02(12)°; C(7)-C(4)-C(3) = 132.07(11)°; C(3)-C(6)-C(8) = 131.31(12)°; C(4)-C(7)-C(14) = 122.78(11)°; C(4)-C(7)-C(20) = 121.37(11)°. Selected torsion angles: C(4)-C(3)-C(6)-C(8) = -4.6(2)°; C(3)-C(4)-C(7)-C(14) = -12.8(2)°; C(3)-C(4)-C(7)-C(20) = 168.14(12)°; C(6)-C(3)-C(4)-C(7) = -25.4(2)°.
10. Hunter, C. A.; Lawson, K. R.; Perkins, J.; Urch, C. J. J. Chem. Soc., Perkin Trans. 2 2001, 651-669.
11. Coates, G. W.; Dunn, A. R.; Henling, L. M.; Ziller, J. W.; Lobkovsky, E. B.; Grubbs, R. H. J. Am. Chem. Soc. 1998, 120, 3641-3649.
12. Jones, G. B.; Chapmam, B. J. Synthesis 1995, 475-497.
13. Guckian, K. M.; Schweitzer, B. A.; Ren, R. X.-F.; Sheils, C. J.; Tahmassebi D. C.; Kool, E. T. J. Am. Chem. Soc. 2000, 122, 2213-2222.
14. Viel, S.; Mannina, L.; Segre, A. Tetrahedron Lett. 2002, 43, 2515-2519.
15. 4. Removal of ether in vacuo afforded the diacid as an oil. In dim red light, the diacid was dissolved in acetyl chloride (1.5-2.0 mL) and left at room temperature for 30 min. The extra acetyl chloride was removed in vacuo to give a residue, which was dissolved into a small amount of ethyl acetate (1.0-2.0 mL). The anhydride product was precipitated by addition of hexane.
16. +, 457.