A simple asymmetric synthesis of cis-2,6-disubstituted tetrahydropyran acetic acid derivatives

Tetrahedron Letters

Volumn 38, Issue 6, 1997, Pages 1009-1012

  Edmunds, A J F ^a   Trueb, W ^a  

^a Sandoz Agro AG   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

6 METHYLTETRAHYDROPYRAN 2 YLACETIC ACID; ACETIC ACID DERIVATIVE; TETRAHYDROPYRAN DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; IN VITRO STUDY; METHODOLOGY; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0031562038     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(96)02483-5     Document Type: Article

References (21)

1. 1. Boivin, T. L. B. Tetrahedron, 43, 3309, 1987 and references cited therein.
2. 2. A recent publication has appeared on the role of double bond geometry in controlling the diastereoselectivity of this type of cyclisation. See, Banwell, M.G.; Bui. C.T.; Pham, Ha-T. T.; Simpson, G.W. J. Chem. Soc. Perkin Trans. I,, 1996, 967.
3. 3. For the first example of this type of strategy see a) Seebach, D.; Pohmaktor, M.S. Helv. Chim. Acta, 1979, 62, 1096. For other examples see
4. b) Kocienski, P. J.; Smith, N. D.; Street, S. D. A. Synthesis, 1996, 652.
5. c) Banwell, M. G.; Bui, C. T.; Simpson G. W.; Watson, K.G. Chem. Commun., 1996, 723.
6. d) Machinaga, N.; Kibayashi, C. Tetrahedron Lett., 1993, 34, 5739.
7. e) Palazon, J. M.; Soler, M. A.; Ramirez, M. A.; Martin, S.V. Tetrahedron Lett, 1993, 34, 5467. Intramolecular 1,4-addition of oxyanions to tethered chiral α,β-unsaturated sulfoxides has been used as an approach to prepare 2,6-disubstituted tetrahydropyrans in a diastereoselective manner.
8. See; f) Mandai, T.; Ueda, M.; Kashiwagi., K.; Kawada, M.; Tsuji, J. Tetrahedron Lett., 1993, 34, 111.
9. 4. Mancuso, J.A.; Swern, D. Synthesis, 1981, 165.
10. 1H NMR and GC/MS showed a ratio of ≥ 95:5 of E:Z isomers.
11. 6. Van Rheenen, V.; Kelly, R.C.; Cha, D.Y. Tetrahedron Lett, 1976, 1973.
12. 3OD) 22.83; 33.98; 34.03; 34.06; 34.11; 52.53; 67.25; 73.02; 73.06; 73.53; 74.76; 74.80; 175.27 ppm.
13. 8. a) Kolb, H.C.; Van Nieuwenhze, M.S.; Sharpless, K.B. Chem.Rev., 1994, 94, 2483.
14. b) Sharpless K.B.; Amberg, W.; Bennani, Y.L.; Crispino, G.; Harrtung, J.; Jeong, K.-S.; Kwong, H.-L.; Morikawa, K.; Wang, Z.-M.; Xn, D.; Zhang, X.-L. J.Org.Chem., 1992, 57, 2678.
15. c). Crispino, G.; Jeong, K.-S.; Kolb, H.C.; Wang, Z.-M.; Xn, D.; Sharpless, K. B. J.Org.Chem., 1993, 55, 3785.
16. 1H NMR analysis of the racemic sample showed signals for the β-olefinic protons (dt, J = 15.6, 1.5 Hz) at 5.808 (t), 5.758 (q) and 5.715 ppm (t). The enantiomer ratios were thus determined by integration of the triplets at 5.808 and 5.715 ppm in the non-racemic samples.
17. 10. This phenomenon is usually observed. See reference 8a.
18. 11. Maurer, B.; Grieder, A.; Thommen, W. Helv. Chim. Acta, 1979, 62, 44. For syntheses see: Ragoussis, V.; Theodorou, V. Synthesis, 1993, 84 and references cited therein.
19. 11. Maurer, B.; Grieder, A.; Thommen, W. Helv. Chim. Acta, 1979, 62, 44. For syntheses see: Ragoussis, V.; Theodorou, V. Synthesis, 1993, 84 and references cited therein.
20. 12. The conversion 6 to 9 is analogous to that reported by: Jones, J.B.; Hinks, R.S. Can. J. Chem., 1987, 65, 704.
21. 13. Mitsunobu, O. Synthesis, 1981, 1.