82105-33-7Relevant academic research and scientific papers
Tandem one-pot Wittig/reductive aldol reactions in which the waste from one process catalyzes a subsequent reaction
Lu, Jinni,Toy, Patrick H.
, p. 2251 - 2254 (2011)
Putting waste to work: Tandem one-pot Wittig/reductive aldol reactions have been performed in which the byproduct of the Wittig reaction, Ph3PO, catalyzes the reductive aldol reaction. This methodology is versatile and allows for three different building blocks to be combined in a simple, one-pot procedure. Copyright
A New Protocol for Regio- and Stereocontrolled Aldol Reactions through the Conjugate Addition of Dialkylboranes to α,β-Unsaturated Ketones
Boldrini, Gian Paolo,Bortolotti, Michele,Mancini, Fabrizio,Tagliavini, Emilio,Trombini, Claudio,Umani-Ronchi, Achille
, p. 5820 - 5826 (2007/10/02)
A one-pot, two-step procedure, consisting of the 1,4-addition of dialkylboranes to β-substituted (E)-α,β-unsaturated ketones followed by the reaction of the resulting configurationally pure (Z)-(vinyloxy)boranes with aldehydes, is reported.The overall process corresponds to a regio- and stereocontrolled aldol addition of an unsymmetrical ketone to an aldehyde.A concerted 1,4-addition mechanism accounts for the stereochemical outcome of the hydroboration reaction; cyclic enones do not undergo conjugate addition, while (Z)-β-substituted or β,β-disubstituted α,β-unsaturated ketones still react in a 1,4-fashion, but with a slower rate and a lower degree of chemoselectivity with respect to β-substituted (E)-α,β-unsaturated ketones.In the cases of α,β-disubstituted α,β-unsaturated ketones and (E)-(S-phenylthio)cinnamate, which react with dicyclohexylborane to give a mixture of E and Z enolates, an alternative mechanism is proposed.
A New Approach to (Z)-Vinyloxyboranes via 1,4 Hydroboration of (E)-α,β-Unsaturated Ketones. Synthesis of syn Aldols
Boldrini, Gian Paolo,Mancini, Fabrizio,Tagliavini, Emilio,Trombini, Claudio,Umani-Ronchi, Achille
, p. 1680 - 1681 (2007/10/02)
(Z)-Vinyloxy boranes are obtained via 1,4-hydroboration of acyclic disubstituted (E)-α,β-unsaturated ketones with dicyclohexylborane or diisopinocampheylborane in tetrahydrofuran, CH2Cl2 or CHCl3 at 20 deg C; treatment of the hydroboration mixture with an aldehyde allows pure syn aldols to be synthesized in good yields, and in excellent enantiomeric excesses, using the latter borane.
A NEW METHOD FOR THE REGIO- AND STEREOSELECTIVE SYNTHESIS OF ALDOLS FROM α-BROMOKETONE AND CARBONYL COMPOUNDS BY USING METALLIC TIN
Harada, Taira,Mukayiama, Teruaki
, p. 467 - 470 (2007/10/02)
Tin(II) enolates, generated in situ by the oxidative addition of α-bromoketones to metallic tin, react with a variety of carbonyl compounds under mild conditions to give the corresponding aldols in good yields.In the case of reactions of the enolate resul
