Lewis Acid-Catalyzed Ring-Opening Reactions of Semicyclic N,O-Acetals Possessing an Exocyclic Nitrogen Atom:  Mechanistic Aspect and Application to Piperidine Alkaloid Synthesis

Author:

Sugiura Masaharu1,Hagio Hiroyuki1,Hirabayashi Ryoji1,Kobayashi Shū1

Affiliation:

1. Contribution from Graduate School of Pharmaceutical Sciences, The University of Tokyo, CREST, Japan Science and Technology Corporation (JST), Hongo, Bunkyo-ku, Tokyo 113-0033, Japan

Publisher

American Chemical Society (ACS)

Subject

Colloid and Surface Chemistry,Biochemistry,General Chemistry,Catalysis

Reference45 articles.

1. Gabbutt, C. D.; Hepworth, J. D. InComprehensive Organic FunctionalGroup Transformations; Katritzky, A. R., Meth-Cohn, O., Rees, C. W., Eds.; Kirby, G. W., Volume Ed.; Pergamon:  Oxford, 1995; Vol. 4, pp 293−349.

2. Protective Groups in Organic Synthesis

3. Recent advances in stereoselective c-glycoside synthesis

4. Endocyclic cleavage in acid-catalyzed methanolysis and hydrolysis of a pyranoside (a semicyclicO,O-acetal) has been reported; (a) Liras, J. L.; Anslyn, E. V. InMolecular Design and Bioorganic Catalysis; Wilcox, C. S., Hamilton, A. D., Eds.; NATO SAI Ser.; Kluwer Academic Publishers:  Boston, MA, 1996; Vol. 478, pp 1−15. (b) Liras, J. L.; Anslyn, E. V.J. Am.Chem. Soc.1994,116, 2645.

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