Linear aminopolyhydroxylated structures through rapid domino assembly of a highly functionalized heterotricyclic system and its selective cleavage

Chemistry - A European Journal

Volumn 4, Issue 12, 1998, Pages 2501-2512

  Righi, Paolo ^a   Marotta, Emanuela ^a   Rosini, Goffredo ^a  

^a UNIVERSITY OF BOLOGNA   (Italy)

Author keywords

Amino alcohols; Cycloadditions; Domino reactions; Heterocycles; Tandem reactions

Indexed keywords

4 HYDROXY 2 ISOXAZOLINE 2 OXIDE DERIVATIVE; NITROALKANE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; CYCLIZATION; HYDROXYLATION; MOLECULAR RECOGNITION; REACTION ANALYSIS; REDUCTION; STRUCTURE ANALYSIS;

EID: 0031796184     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3765(19981204)4:12<2501::AID-CHEM2501>3.0.CO;2-I     Document Type: Article

References (39)

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4. Throughout this paper the term tandem has been used according to the definition given by T.-L. Ho, Tandem Organic Reactions, Wiley, New York, 1992; p. 1.
5. Suitable electrophiles for this reactions are: a) α,β-epoxy aldehydes (G. Rosini, R. Galarini, E. Marotta, P. Righi, J. Org. Chem. 1990, 55, 781-783); b) α-bromo aldehydes (G. Rosini, E. Marotta, P. Righi, J.-P. Seerden, J. Org. Chem. 1991, 56, 6258-6260); c) α-bromo enones (G. Rosini, E. Marotta, P. Righi, C. Galli, J. Org. Chem. 1995, 60, 6624-6626).
6. Suitable electrophiles for this reactions are: a) α,β-epoxy aldehydes (G. Rosini, R. Galarini, E. Marotta, P. Righi, J. Org. Chem. 1990, 55, 781-783); b) α-bromo aldehydes (G. Rosini, E. Marotta, P. Righi, J.-P. Seerden, J. Org. Chem. 1991, 56, 6258-6260); c) α-bromo enones (G. Rosini, E. Marotta, P. Righi, C. Galli, J. Org. Chem. 1995, 60, 6624-6626).
7. Suitable electrophiles for this reactions are: a) α,β-epoxy aldehydes (G. Rosini, R. Galarini, E. Marotta, P. Righi, J. Org. Chem. 1990, 55, 781-783); b) α-bromo aldehydes (G. Rosini, E. Marotta, P. Righi, J.-P. Seerden, J. Org. Chem. 1991, 56, 6258-6260); c) α-bromo enones (G. Rosini, E. Marotta, P. Righi, C. Galli, J. Org. Chem. 1995, 60, 6624-6626).
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16. G. Stork, J. J. La Clair, J. Am. Chem. Soc. 1996, 118, 247-248; G. Stork, T. Y. Chan, G. A. Breault, J. Am. Chem. Soc. 1992, 114, 7578-7579; G. Stork, G. Kim, J. Am. Chem. Soc. 1992, 114, 1087-1088; G. Stork, H. S. Suh, G. Kim, J. Am. Chem. Soc. 1991, 113, 7054-7056. It has been recently reported that also magnesium or aluminum can serve as temporary tethers: G. Stork, T. Y. Chan, J. Am. Chem. Soc. 1995, 117, 6595-6596.
17. G. Stork, J. J. La Clair, J. Am. Chem. Soc. 1996, 118, 247-248; G. Stork, T. Y. Chan, G. A. Breault, J. Am. Chem. Soc. 1992, 114, 7578-7579; G. Stork, G. Kim, J. Am. Chem. Soc. 1992, 114, 1087-1088; G. Stork, H. S. Suh, G. Kim, J. Am. Chem. Soc. 1991, 113, 7054-7056. It has been recently reported that also magnesium or aluminum can serve as temporary tethers: G. Stork, T. Y. Chan, J. Am. Chem. Soc. 1995, 117, 6595-6596.
18. G. Stork, J. J. La Clair, J. Am. Chem. Soc. 1996, 118, 247-248; G. Stork, T. Y. Chan, G. A. Breault, J. Am. Chem. Soc. 1992, 114, 7578-7579; G. Stork, G. Kim, J. Am. Chem. Soc. 1992, 114, 1087-1088; G. Stork, H. S. Suh, G. Kim, J. Am. Chem. Soc. 1991, 113, 7054-7056. It has been recently reported that also magnesium or aluminum can serve as temporary tethers: G. Stork, T. Y. Chan, J. Am. Chem. Soc. 1995, 117, 6595-6596.
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22. [8] The numbering in Scheme 3 refers to this name. We suggest the use of the acronym HFTS in place of this awkward IUPAC name.
23. For a preliminary communication see: P. Righi, E. Marotta, A. Landuzzi, G. Rosini, J. Am. Chem. Soc. 1996, 118, 9446-9447.
24. Performed as implemented in Chem3D Pro (Ser. #495965). CambridgeSoft, Cambridge, MA 02139 (USA).
25. 2 substituents of the compound as shown in Table 2.
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27. For reviews on domino reactions see: L. F. Tietze, Chem. Rev. 1996, 96, 115-136; L. F. Tietze, U. Beifuss, Angew. Chem. 1993, 105, 137-169; Angew. Chem. Int. Ed. Engl. 1993, 32, 131-163.
28. For reviews on domino reactions see: L. F. Tietze, Chem. Rev. 1996, 96, 115-136; L. F. Tietze, U. Beifuss, Angew. Chem. 1993, 105, 137-169; Angew. Chem. Int. Ed. Engl. 1993, 32, 131-163.
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37. [27]
38. S. E. Denmark, A. Thorarensen, J. Org. Chem. 1994, 59, 5672-5680.
39. This value was calculated following: S. H. Bertz, T. J. Sommer, Applications of Graph Theory to Synthesis Planning: Complexity, Reflexivity, and Vulnerability. In Organic Synthesis: Theory and Applications. Vol. 2, (Ed.: T. Hudlicky), JAI, Greenwich, CT, 1993, p. 67-92.