Scope and Limitation of Organocuprates, and Copper or Nickel Catalyst-Modified Grignard Reagents for Installation of an Alkyl Group onto cis-4-Cyclopentene-1,3-diol Monoacetate

Author:

Ito Michiko1,Matsuumi Michitaka1,Murugesh Modachur G.1,Kobayashi Yuichi1

Affiliation:

1. Department of Biomolecular Engineering, Tokyo Institute of Technology, 4259 Nagatsuta-cho, Midori-ku, Yokohama 226-8501, Japan

Publisher

American Chemical Society (ACS)

Subject

Organic Chemistry

Reference47 articles.

1. (1R,3S)-1:  (a) Deardorff, D. R.; Amador, R. B.; Morton, J. W.; Kim, H. Y.; Taniguchi, C. M.; Balbuena, A. A.; Warren, S. A.; Fanous, V.; Choe, S. W. T.Tetrahedron:  Asymmetry1999,10, 2139−2152. (b) Deardorff, D. R.; Windham, C. Q.; Craney, C. L. InOrganic Syntheses; Freeman, J. P., Ed.; Wiley:  New York, 1998; Collect. Vol. 9, pp 487−493. (c) Johnson, C. R.; Bis, S. J.Tetrahedron Lett.1992,33, 7287−7290. (d) Sugai, T.; Mori, K.Synthesis1988, 19−22. (e) Deardorff, D. R.; Matthews, A. J.; McMeekin, D. S.; Craney, C. L.Tetrahedron Lett.1986,27, 1255−1256. (f) Laumen, K.; Schneider, M. P.J. Chem. Soc., Chem. Commun.1986, 1298−1299. (1S,3R)-1:  (g) Ghorpade, S. R.; Kharul, R. K.; Joshi, R. R.; Kalkote, U. R.; Ravindranathan, T.Tetrahedron:  Asymmetry1999,10, 891−899. (h) Johnson, C. R.; Braun, M. P.J. Am. Chem. Soc.1993,115, 11014−11015. (i) Theil, F.; Schick, H.; Winter, G.; Reck, G.Tetrahedron1991,47, 7569−7582. (j) Theil, F.; Ballschuh, S.; Schick, H.; Haupt, M.; Häfner, B.; Schwarz, S.Synthesis1988, 540−541. (k) Theil, F.; Schick, H.; Lapitskaya, M. A.; Pivnitsky, K. K.Liebigs Ann. Chem.1991, 195−200. (l) Laumen, K.; Reimerdes, E. H.; Schneider, M.Tetrahedron Lett.1985,26, 407−410. (m) Laumen, K.; Schneider, M.Tetrahedron Lett.1984,25, 5875−5878. (n) Wang, Y.F.; Chen, C.S.; Girdaukas, G.; Sih, C. J.J. Am. Chem. Soc.1984,106, 3695−3696.

2. 4-Oxo-2-cyclopentenyl Acetate?A Synthetic Intermediate

3. Coupling reaction of 4-cyclopentene-1,3-diol monoacetate and lithium alkenylborates and its application to chiral synthesis of prostaglandin intermediates

4. Enantioselective preparation of functionalized cyclopentanoids via a common chiral (.pi.-allyl)palladium complex

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