Studies of intramolecular cyclizations of N-acyliminium ions derived from acyclic ketones: Unanticipated stereochemical and structural results

Organic Letters

Volumn 5, Issue 16, 2003, Pages 2915-2918

  Chao, Wenchun ^a   Waldman, Jacob H ^a   Weinreb, Steven M ^a  

^a PENNSYLVANIA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE DERIVATIVE; IMINE; ION; KETONE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CYCLIZATION; CYCLOADDITION; DIELS ALDER REACTION; GEOMETRY; MOLECULAR INTERACTION; STEREOCHEMISTRY; X RAY ANALYSIS;

KETONES; STEREOISOMERISM;

EID: 0141631601     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol035046m     Document Type: Article

References (28)

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2. For extensive reviews of the chemistry of N-acylimines and iminium ions, see: (a) Speckamp, W. N.; Hiemstra, H. Tetrahedron 1985, 41, 4367. (b) Hiemstra, H.; Speckamp, W. N. In N-Acyliminium Ions as Intermediates in Alkaloid Synthesis In The Alkaloids; Brossi, A., Ed.; Academic Press: New York, 1988; Vol. 32, p 271. (c) Hiemstra, H.; Speckamp, W. N. Additions to N-Acyl Iminium Ions. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 2, p 1047. (d) Speckamp, W. N.; Moolenaar, M. J. Tetrahedron 2000, 56, 3817.
3. For extensive reviews of the chemistry of N-acylimines and iminium ions, see: (a) Speckamp, W. N.; Hiemstra, H. Tetrahedron 1985, 41, 4367. (b) Hiemstra, H.; Speckamp, W. N. In N-Acyliminium Ions as Intermediates in Alkaloid Synthesis In The Alkaloids; Brossi, A., Ed.; Academic Press: New York, 1988; Vol. 32, p 271. (c) Hiemstra, H.; Speckamp, W. N. Additions to N-Acyl Iminium Ions. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 2, p 1047. (d) Speckamp, W. N.; Moolenaar, M. J. Tetrahedron 2000, 56, 3817.
4. For extensive reviews of the chemistry of N-acylimines and iminium ions, see: (a) Speckamp, W. N.; Hiemstra, H. Tetrahedron 1985, 41, 4367. (b) Hiemstra, H.; Speckamp, W. N. In N-Acyliminium Ions as Intermediates in Alkaloid Synthesis In The Alkaloids; Brossi, A., Ed.; Academic Press: New York, 1988; Vol. 32, p 271. (c) Hiemstra, H.; Speckamp, W. N. Additions to N-Acyl Iminium Ions. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 2, p 1047. (d) Speckamp, W. N.; Moolenaar, M. J. Tetrahedron 2000, 56, 3817.
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23. We thank Dr. Louis Todaro (Hunter College) for the X-ray determination of carbamate 12 and Dr. Hemant Yennawar (Penn State Small Molecule X-ray Crystallographic Facility) for the structures of compounds 15, 20, 23, 24, and 29.
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