6090-15-9Relevant academic research and scientific papers
Intramolecular hydroalkoxylation catalyzed inside a self-assembled cavity of an enzyme-like host structure
Catti,Tiefenbacher
supporting information, p. 892 - 894 (2015/02/05)
Self-assembled resorcin[4]arene hexamer catalyzes the intramolecular hydroalkoxylation of unsaturated alcohols to the corresponding cyclic ethers under mild conditions. The mode of catalysis and encapsulation-based substrate selectivity of the host efficiently mimic the basic principle of operation observed in enzymes.
Palladium(II)-catalyzed cyclization of unsaturated hydroperoxides for the synthesis of 1,2-dioxanes
Harris, Jason R.,Waetzig, Shelli R.,Woerpel
experimental part, p. 3290 - 3293 (2009/12/05)
The cyclization of γ, δ-unsaturated tertiary hydroperoxides in the presence of a palladium(II) catalyst afforded 1,2-dioxanes resembling biologically active natural products. A variety of substrates were screened, and synthetic manipulations were accomplished to construct compounds with structural similarity to antimalarial targets.
Organocatalysis in a synthetic receptor with an inwardly directed carboxylic acid
Shenoy, Siddhartha R.,Pinacho Crisostomo, Fernando R.,Iwasawa, Tetsuo,Rebek Jr., Julius
, p. 5658 - 5659 (2008/12/21)
A cavitand functionalized with a Kemp-s triacid derivative was used to catalyze the epoxide ring-opening cyclizations of 1,5-epoxyalcohols. A deep, cylindrical cavity containing electron-rich aromatic walls and an inwardly directed carboxylic acid displayed the necessary characteristics to bind different 1,5-epoxyalcohols and initiate their cyclization reactions. The reactions inside this synthetic receptor occurred in a catalytic and regioselective manner. These results highlight that the arrangement of functionality and unique solvation provided by the structured interiors of natural enzymes can be incorporated into synthetic systems having useful physical and chemical properties. Copyright
Unprecedented stereochemical control in the intramolecular ene-reactions of δ,ε-unsaturated aldehydes using exceptionally bulky organoaluminum reagents: Elucidation of the transition state
Ooi,Maruoka,Yamamoto
, p. 6505 - 6522 (2007/10/02)
Unprecendented stereochemical control has been achieved in the type II intramolecular ene reactions of δ,ε-unsaturated aldehydes leading to trans-cyclohexanols with excellent selectivity under very mild conditions, using exceptionally bulky methylaluminum bis(4-bromo-2,6-di-tert-butylphenoxide) (MABR). Success of the stereocontrolled cyclization can be ascribable to the ability of this modified organoaluminum reagents, MABR, to change the conformation of the transition state. Examining the ene reactions of substrates 7, 11, 14 with MABR, the stereochemical outcome of the present organoaluminum-promoted intramolecular ene reactions is further elucidated.
Sandalwood odorants
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, (2008/06/13)
The present invention relates to novel substituted cyclohexanol compounds possessing a sandalwood aroma which are useful as fragrance materials. The invention also provides methods for synthesis thereof through a novel aldehyde intermediate. The compounds of the invention have the formula: STR1 wherein A is STR2 and wherein R1 is methyl or ethyl, R2 -R7 are independently hydrogen or methyl with the proviso that a maximum of two of the substituents R2 -R7 are methyl, and R8 is hydrogen, lower alkyl (C1 to C5) or acyl. The invention also provides fragrance compositions which utilize the compounds of the invention to impart a sandalwood aroma to perfume compositions, colognes and perfumed articles.
Functionalization of terminal trisubstituted alkenes and derivatives thereof
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, (2008/06/13)
The invention relates to a process for preparing compounds having the general structure: STR1 wherein R is hydrogen or an acyclic or alicyclic fragment containing between one and about ten carbon atoms, and R1 is hydrogen or an alkyl containing between one and about four carbon atoms or an aryl group.
