Polymer-aided stereodivergent synthesis (PASS): A new concept for the discrete preparation of optical antipodes

Organic Letters

Volumn 3, Issue 7, 2001, Pages 1093-1095

  Ten Holte, Peter ^a   Thijs, Lambertus ^a   Zwanenburg, Binne ^a  

^a RADBOUD UNIVERSITY NIJMEGEN   (Netherlands)

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EID: 0000566351     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol015723h     Document Type: Article

References (23)

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10. (a) Bakke, M.; Takizawa, M.; Sugai, T.; Ohta, H. J. Org. Chem. 1998, 63, 6929.
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12. (a) Vries, T.; Wynberg, H.; van Echten, E.; Koek, J.; ten Hoeve, W.; Kellogg, R. M.; Broxterman, Q. B.; Minaard, A.; Kaptein, B.; van der Sluis, S.; Hulshof, L.; Kooistra, J. Angew. Chem. Int. Ed. 1998, 37, 2349.
13. (b) Vannieuwenhze, M. S.; Sharpless, K. B. J. Am. Chem. Soc. 1993, 115, 7864.
14. According to the 1996 IUPAC recommendations, quasi-enantiomers are defined as "constitutionally different yet closely related chemical species MX and MY having the opposite chirality sense of the large common chiral moiety, M."
15. ten Holte, P.; Thijs, L.; Zwanenburg, B. Tetrahedron Lett. 1998, 39, 7407.
16. AX = 3.8 Hz), 3.74 (bs, 2H), 3.93 (m, 1H), 4.03 (m, 2H), 7.34 (d, 2H, J = 8.2 Hz), 7.78 (d, 2H, J = 8.3 Hz) ppm. Melting point and spectral data are in agreement with those reported: Baldwin, J. J.; Raab, A. W.; Mensler, K.; Arison, B. H.; McClure, D. E. J. Org. Chem. 1978, 43, 4876.
17. Unreacted 1,2-diol 6 was readily recovered by filtration and subsequent flash column chromatographic purification (ethyl acetate/hexane = 1/1, v/v, 250 mL followed by ethyl acetate) of the concentrated filtrate.
18. PS-TsCl, 1.34 mequiv/g, Argonaut Technologies Inc.
19. 3) δ 44.47, 48.15, 70.80, 118.31, 124.38, 129.13, 137.76, 153.87.
20. 3) δ 44.48, 48.15, 70.80, 118.32, 124.39, 129.13, 137.76, 153.86 ppm.
21. 3) δ 47.44, 53.03, 70.54, 118.27, 124.34, 129.13, 137.83, 153.90 ppm.
22. 3, 75 MHz): δ 47.44, 53.04, 70.54, 118.28, 124.35, 129.14, 137.84, 153.93 ppm.
23. 1H NMR, and melting point of 13 are in aggreement with those reported: Gregory, W. A.; Brittelli, D. R.; Wang, C.-L. J.; Wuonola, M. A.; McRipley, R. J.; Eustice, D. C.; Eberly, V. S.; Barthohomew, P. T.; Slee, A. M.; Forbes, M. J. Med. Chem. 1989, 32, 1673.