Diastereo-differentiating coupling of phenoxy radical moiety controlled by 2,4-pentanediol tether: Preparation of optically active Pummerer's ketone analogs
Yamaguchi, K.; Sugimura, T.; Nishida, F.; Tai, A.
Tetrahedron Letters 39(25): 4521-4524
1998
ISSN/ISBN: 0040-4039 DOI: 10.1016/s0040-4039(98)00805-3
Accession: 008462269
The highly diastereo-differentiating coupling of the phenoxy radical could be achieved by a 2,4-pentanediol tethered reaction to give a single diastereomer of Pummerer's ketone analog. By the removal of the chiral auxiliary, the optically active phenoxy radical dimer was obtained in good yield.
PDF emailed within 0-6 h: $19.90
Related References
Mori, A.; Sugimura, T.; Tai, A. 1997: Diastereo-differentiating intramolecular cyclopropanations of prochiral olefins and a diazo ester linked by optically active 2,4-pentanediol Tetrahedron: Asymmetry 8(5): 661-664Sugimura, T.; Nagano, S.; Tai, A. 1998: The first Asymmetric Synthesis of Optically Active Tropilidenes. Highly Regio- and Diastereo-differentiating Addition of Diazo Ester to Aromatic Ring Using 2,4-Pentanediol as Chiral Linking Bridge Chemistry Letters 27(1): 45-46
Ito, K.; Harada, T.; Tai, A.; Izumi, Y. 1979: A Facile Method for the Preparation of Optically Pure 2,4-Pentanediol; An Application of Asymmetrically Modified Nickel Catalyst for the Preparation of Optically Active Compounds Chemistry Letters 8(9): 1049-1050
Sugimura, T.; Nishiyama, N.; Tai, A.; Hakushi, T. 1993: Diastereoface differentiating peracid oxidation of the enol ether derived from cyclohexanone and 2,4-pentanediol : preparation of optically pure 2-hydroxycyclohexanone acetal Tetrahedron : Asymmetry 4(1): 43-44
Sugimura, T.; Iguchi, H.; Tsuchida, R.; Tai, A.; Nishiyama, N.; Hakushi, T. 1998: Diastereoface-differentiating oxidation of 1-cyclohexenyl ether using a 2,4-pentanediol tether Tetrahedron: Asymmetry 9(6): 1007-1013
Sugimura, T.; Futagawa, T.; Tai, A. 1988: Diastereo-differentiating Simmons-Smith reaction using 2,4-pentanediol as achiral auxiliary Tetrahedron Letters 29(45): 5775-5778
Sugimura, T.; Yoshikawa, M.; Futagawa, T.; Tai, A. 1990: Diastereo-differentiating cyclopropanation of a chiral enol ether : a simple method for the preparation of optically pure cyclopropyl ethers Tetrahedron (Oxford. Print) 46(17): 5955-5966
Terashima, S.; Tamoto, K. 1983: A novel racemization mechanism for the α-hydroxy ketone moiety(C9-position) of optically active anthracyclinone derivatives Tetrahedron Letters 24(25): 2589-2592
Dafforn, A.; Neenan, J.P.; Ash, C.E.; Betts, L.; Finke, J.M.; Garman, J.A.; Rao, M.; Walsh, K.; Williams, R.R. 1982: Acetylcholinesterase inhibition by the ketone transition state analog phenoxyacetone and 1-halo-3-phenoxy-2-propanones Biochemical and Biophysical Research Communications 104(2): 597-602
Tamoto, K; Terashima, S 1984: Elucidation of the racemization mechanism of the .ALPHA.-hydroxy ketone moiety (C9-position) of optically active anthracyclinone derivatives Chemical and Pharmaceutical Bulletin 32(11): 4340-4349
Tamoto, K.; Terashima, S. 1984: Elucidation of the racemization mechanism of the alpha hydroxy ketone moiety carbon 9 position of optically active anthracyclinone derivatives Chemical and Pharmaceutical Bulletin 32(11): 4340-4349
Hagiya, K.; Yamasaki, A.; Okuyama, T.; Sugimura, T. 2004: Asymmetric meta-arene–alkene photocycloaddition controlled by a 2,4-pentanediol tether Tetrahedron: Asymmetry 15(9): 1409-1417
Im, C.Y.; Okuyama, T.; Sugimura, T. 2005: Stereoselective Intramolecular O–H Insertion of Rhodium Carbenoid Controlled by the 2,4-Pentanediol Tether Chemistry Letters 34(10): 1328-1329
Nakade, H.; Obata, M.; Tsuji, M.; Narumi, A.; Satoh, T.; Yokota, K.; Kakuchi, T. 2001: Chirality induction in cyclopolymerization. XVI. Synthesis of optically active poly(methyl acrylate-co-dimethyl fumarate) by radical cyclopolymerization of asymmetrical nonconjugated diene having chiral pentanediol Polymer Journal 33(12): 946-951
Tamboli, A.B.; Maldar, N.N. 2020: Synthesis and characterization of processable aromatic poly(ether ether ketone amide)s modified by phenoxy and 1,3 ketone moiety linkages Polymer Bulletin 77(12): 6591-6605
Wu, S.; Yang, N.; Liu, Y.; Cao, J.; Hu, H.; Sun, Y.; Liu, J. 2010: Optically active helical polymer from radical polymerization of menthyl vinyl ketone Journal of Polymer Science Part A: Polymer Chemistry 49(1): 293-299
Shi, W.U.; Nianfa, Y.A.N.G.; Yanling, L.I.U.; Jing, C.A.O.; Hai, H.U.; Yunkai, S.U.N.; Ji, L.I.U. 2011: Optically Active Helical Polymer from Radical Polymerization of Menthyl Vinyl Ketone Journal of Polymer Science. Part A. Polymer Chemistry 49(1): 293-299
Tănase, C.I.; Drăghici, C.; Hanganu, A.; Pintilie, L.; Maganu, M.; Volobueva, A.; Sinegubova, E.; Zarubaev, V.V.; Neyts, J.; Jochmans, D.; Slita, A.V. 2019: New HSV-1 Anti-Viral 1'-Homocarbocyclic Nucleoside Analogs with an Optically Active Substituted Bicyclo[2.2.1]Heptane Fragment as a Glycoside Moiety Molecules 24(13)
Davin, L.B.; Wang, H.B.; Crowell, A.L.; Bedgar, D.L.; Martin, D.M.; Sarkanen, S.; Lewis, N.G. 1997: Stereoselective bimolecular phenoxy radical coupling by an auxiliary (dirigent) protein without an active center Science 275(5298): 362-366
Lim, M.I.; Marquez, V.E. 1983: A synthetic approach towards neplanocin A: preparation of the optically active cyclopentene moiety from D-ribose Tetrahedron Letters 24(38): 4051-4054