Mg2+-Imidazole-Catalyzed Self-Condensation of Malonyl Thioesters: Getting Tuned for Biomimetic Polyketide Synthesis?
N Sakai, N Sordé, S Matile
Index: Sakai, Naomi; Sorde, Nathalie; Matile, Stefan Molecules, 2001 , vol. 6, # 11 p. 845 - 851
Full Text: HTML
Citation Number: 19
Abstract
Abstract: We report that a subtle balance of carbanion reactivity, leaving group activation, and p K a of the catalyst is required for efficient self-condensation of thiomalonates to thioacetoacetates in up to 71% yield under “biomimetic” conditions originally proposed by Kobuke and Yoshida (Tetrahedron Lett. 1978, 19, 367).
Related Articles:
[Imamoto, Tsuneo; Kodera, Masahito; Yokoyama, Masataka Bulletin of the Chemical Society of Japan, 1982 , vol. 55, # 7 p. 2303 - 2304]
[Bae, Han Yong; Sim, Jae Hun; Lee, Ji-Woong; List, Benjamin; Song, Choong Eui Angewandte Chemie - International Edition, 2013 , vol. 52, # 46 p. 12143 - 12147 Angew. Chem., 2013 , vol. 125, # 46 p. 12365 - 12369,5]
A convenient one-pot procedure for synthesis of thiol esters using magnesium ion as a catalyst
[Ohta, Shunsaku; Okamoto, Masao Tetrahedron Letters, 1981 , vol. 22, # 34 p. 3245 - 3246]
Action de Dérivés Maloniques sur les Thio et Sélénophénols
[Ruwet,A. et al. Bulletin des Societes Chimiques Belges, 1970 , vol. 79, p. 631 - 637]