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Volumn 128, Issue 51, 2006, Pages 16480-16481

A Sakurai-Prins-Ritter sequence for the three-component diastereoselective synthesis of 4-amino tetrahydropyrans

Author keywords

[No Author keywords available]

Indexed keywords

AMINE; TETRAHYDROPYRAN DERIVATIVE;

EID: 33845953429     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja066794k     Document Type: Article
Times cited : (86)

References (50)
  • 1
    • 33750173220 scopus 로고
    • Reviews on multicomponent reactions: a
    • Reviews on multicomponent reactions: (a) Tietze, L. F.; Beifuss, U. Angew. Chem., Int. Ed. 1993, 32, 131.
    • (1993) Angew. Chem., Int. Ed , vol.32 , pp. 131
    • Tietze, L.F.1    Beifuss, U.2
  • 19
    • 0037016467 scopus 로고    scopus 로고
    • For similar approaches to 4-methylene tetrahydropyrans see
    • For similar approaches to 4-methylene tetrahydropyrans see: Yu, C.-M.; Lee, J.-Y.; So, B.; Hong, J. Angew. Chem., Int. Ed. 2002, 41, 161.
    • (2002) Angew. Chem., Int. Ed , vol.41 , pp. 161
    • Yu, C.-M.1    Lee, J.-Y.2    So, B.3    Hong, J.4
  • 23
    • 33845937370 scopus 로고    scopus 로고
    • Reviews on a Prins cyclization: Snider, B. B. In The Prins Reaction and Carbonyl Ene Reactions; Trost, B. M., Fleming, I., Heathcock, C. H., Eds.; Pergamon Press: New York, 1991; 2, pp 527-561.
    • Reviews on a Prins cyclization: Snider, B. B. In The Prins Reaction and Carbonyl Ene Reactions; Trost, B. M., Fleming, I., Heathcock, C. H., Eds.; Pergamon Press: New York, 1991; Vol. 2, pp 527-561.
  • 26
    • 0034624586 scopus 로고    scopus 로고
    • For examples of natural products and related compounds, containing 4-aminotetrahydropyran moiety see: Snider, B. B, Hawryluk, N. Org. Lett. 2000, 2, 635
    • For examples of natural products and related compounds, containing 4-aminotetrahydropyran moiety see: Snider, B. B.; Hawryluk, N. Org. Lett. 2000, 2, 635.
  • 30
    • 0001162607 scopus 로고    scopus 로고
    • Two examples of the use of a Ritter reaction to terminate a Prins cyclization have appeared: (a) Perron, F.; Albizati, K. F. J. Org Chem. 1987, 52, 4128.
    • Two examples of the use of a Ritter reaction to terminate a Prins cyclization have appeared: (a) Perron, F.; Albizati, K. F. J. Org Chem. 1987, 52, 4128.
  • 35
    • 0030602166 scopus 로고    scopus 로고
    • Trapping of the intermediate cation proceeds in varying selectivity depending on Lewis acid, nucleophile, and substitution pattern across the tetrahydropyran ring. For selected examples, see
    • Trapping of the intermediate cation proceeds in varying selectivity depending on Lewis acid, nucleophile, and substitution pattern across the tetrahydropyran ring. For selected examples, see: Hu, Y.; Skalitzky, D. J.; Rychnovsky, S. D. Tetrahedron Lett. 1996, 37, 8679.
    • (1996) Tetrahedron Lett , vol.37 , pp. 8679
    • Hu, Y.1    Skalitzky, D.J.2    Rychnovsky, S.D.3
  • 45
    • 33646443521 scopus 로고    scopus 로고
    • Puglisi, A.; Lee, A.-L.; Schrock, R. R.; Hoveyda, A. H. Org. Lett. 2006, 8, 1871. (See also ref. 8b.)
    • Puglisi, A.; Lee, A.-L.; Schrock, R. R.; Hoveyda, A. H. Org. Lett. 2006, 8, 1871. (See also ref. 8b.)
  • 46
    • 33845962568 scopus 로고    scopus 로고
    • 2O prior to workup.
    • 2O prior to workup.
  • 47
    • 33845924757 scopus 로고    scopus 로고
    • The transformation generates three new stereocenters for a total of eight possible diastereomers. However, we observe only two isomers GC-MS
    • The transformation generates three new stereocenters for a total of eight possible diastereomers. However, we observe only two isomers (GC-MS).
  • 49
    • 33845929501 scopus 로고    scopus 로고
    • Conducting the reaction between 1a and 2b at -45 °C results in the formation of a 29:71 mixture of axial and equatorial acetamide 3ab.
    • Conducting the reaction between 1a and 2b at -45 °C results in the formation of a 29:71 mixture of axial and equatorial acetamide 3ab.
  • 50
    • 33845960503 scopus 로고    scopus 로고
    • The formation of 8 could arise by intramolecular trapping of the 4-tetrahydropyranyl cation with tethered acetate followed by hydrolysis.
    • The formation of 8 could arise by intramolecular trapping of the 4-tetrahydropyranyl cation with tethered acetate followed by hydrolysis.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.