Diastereoselective Diels-Alder reactions of nonracemic 3- and 4-amino furans bound to polystyrene. A comparison of these reactions to their solution state analogues

Tetrahedron Letters

Volumn 37, Issue 13, 1996, Pages 2133-2136

  Schlessinger, Richard H ^a   Bergstrom, Carl P ^a  

^a UNIVERSITY OF ROCHESTER   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BETULACEAE;

FURAN DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; TECHNIQUE;

EID: 0029879258     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00208-0     Document Type: Article

References (34)

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27. For the preparation of vinylogous urethane lactone 4, see reference 1a.
28. Analytical HPLC analysis of the crude reaction mixture demonstrated that 7 had formed with > 99% de%.
29. ret 7.12 (50% 9), 9.46 (50% ent 9), 95:5-hexane:i-propanol, 0.50 ml/min. Under identical conditions, nonracemic 9 did not exhibit a detectable presence of its racemate.
30. Racemic adduct 10 was prepared in an 88% isolated yield from the corresponding racemic furan and methyl acrylate.
31. For the preparation of the nonracemic 3-amino furanone 12, see reference 1b.
32. A protocol similar to that described in reference 19 was used.
33. Compound 17 was prepared in a 93% crude yield from the corresponding pyrrolidine analogue of 12 and methyl acrylate.
34. All new compounds displayed spectroscopic data consistent with their structural assignments.