ChemInform Abstract: Triisobutylaluminum as a Selective Reducing Agent for the Esters of 9,15‐Diketoprostenoic Acids Opening an Access to the 11‐Deoxyprostaglandins E and F.

Abstract

Treatment of the enediones (I) with excess iBu3Al, depending on the molar ratio (I):iBu3Al chosen and on the temp., affords mixtures of the 15α‐ and 15β‐ols (II) and (III) or of the 9α,15α‐ and 9α,15β‐ols (IV) and (V) in one step.

Novel Asymmetric Alkylation of Aromatic Aldehydes with Triethylaluminum Catalyzed by Titanium·(1,1‘-bi-2-naphthol) and Titanium·(5,5‘,6,6‘,7,7‘,8,8‘-octahydro-1,1‘- bi-2-naphthol) Complexes

“…For example, the reaction of benzaldehyde with triisobutylaluminum gave benzyl alcohol exclusively. The use of triisobutylaluminum as a reducing agent is well established …”

Reactions of acyl phosphonates with organoaluminum reagents: a new method for the synthesis of secondary and tertiary α-hydroxy phosphonates

“…As we expected, only the hydride-donor product-secondary a-hydroxy phosphonate 2o was obtained in 67% yield. 13 When the reaction was repeated at À100 C instead of at 0 C, the yield drop to 32%. We also attempted to carry out the alkynylation of acyl phosphonates by using the triethynylaluminum reagent, which was prepared by following the literature procedure.…”

“…All commercially available reagents were used as received unless otherwise reported. Both 1 H NMR and 13 C NMR spectra were obtained in chloroform-d. 1 H NMR chemical shifts were reported in parts per million, and tetramethylsilane was used as an internal reference. 13 C NMR chemical shifts were reported in parts per million and the chloroform solvent signals were used as an internal reference.…”

“…The copies of 1 H, 13 C, and 31 P NMR and HRMS spectra of these synthesized compounds are presented. Supplementary data associated with this article can be found in online version at doi:10.1016/j.tet.2011.03.036.…”