The First Tandem [2 + 2] Cycloaddition−Michael Reaction Using Ynolates:  Facile Construction of Substituted Carbocycles

Author:

Shindo Mitsuru1,Matsumoto Kenji1,Sato Yusuke1,Shishido Kozo1

Affiliation:

1. Institute for Medicinal Resources, University of Tokushima, and TOREST, Japan Science and Technology Corporation (JST), Sho-machi 1, Tokushima 770-8505, Japan

Publisher

American Chemical Society (ACS)

Subject

Organic Chemistry,Physical and Theoretical Chemistry,Biochemistry

Reference6 articles.

1. A synthesis of ynolates via the cleavage of ester dianions

2. A highly stereoselective synthesis of tri- and tetrasubstituted olefins via ynolates

3. Schölkopf, U.; Hoppe, I.Angew.Chem.Int. Ed. Engl.1975,14, 765. Hoppe, I.; Schölkopf, U.Liebigs Ann. Chem.1979, 219−226. Kowalski, C. J.; Fields, K. W.J. Am. Chem. Soc.1982,104, 321−323. Akai, S.; Kitagaki, S.; Naka, T.; Yamamoto, K.; Tsuzuki, Y.; Matsumoto, K.; Kita, Y.J. Chem. Soc.PerkinTrans.11996, 1705−1709. For examples of β-lactone chemistry, see:  (a) Multzer, J.; Chucholowski, A.Angew.Chem.Int. Ed. Engl.1982,21, 777−778. For reviews, see:  (b) Pons, J.M.; Pommier, A.Synthesis1993, 441−459. (c)Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon:  Oxford, 1991; Vol. 6, pp 342−350.

4. A Novel Tandem [2 + 2] Cycloaddition−Dieckmann Condensation:  Facile One-Pot Process To Obtain 2,3-Disubstituted-2-cycloalkenones from Ynolates

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