62730-80-7

Upstream product

• 2550-26-7 4-Phenyl-2-butanone 
• 100-52-7 benzaldehyde 
• 78-95-5 chloroacetone 
• 55985-68-7 3-bromo-4-phenylbutan-2-one 
• 1896-62-4 (E)-benzalacetone 
• 1024022-50-1 2-benzyl-1-hydroxy-1,1-diphenyl-3-butanone 
• 92694-79-6 4-phenyl-1-(trimethylsilyl)-2-butanone 
• 66581-82-6 4-phenyl-3-(trimethylsilyl)-2-butanone 

Relevant academic research and scientific papers

Tandem one-pot Wittig/reductive aldol reactions in which the waste from one process catalyzes a subsequent reaction

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

Generation of rhodium enolates via retro-aldol reaction and its application to regioselective aldol reaction

Retro-aldol reactions of β-hydroxy ketones take place under rhodium catalysis, leading to regioselective formation of the corresponding rhodium enolates. The enolates react with aldehydes in situ to afford the corresponding aldol adducts in high yields.

A New Protocol for Regio- and Stereocontrolled Aldol Reactions through the Conjugate Addition of Dialkylboranes to α,β-Unsaturated Ketones

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

(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.

Aldol Reactions with α-Trimethylsilyl Ketones. Dual Roles of the Trimethylsilyl Group for Regiospecific Generation of Enolate Equivalents

Aldol reactions of α-trimethylsilyl ketones, R1CH(SiMe3)COCH2R2, with aldehydes or acetals have been examined under Lewis acidic and basic conditions.In the presence of stannic chloride or boron trifluoride etherate, α-trimethylsilyl ketones react with aldehydes or acetals on the carbon bearing the silyl group exclusively to afford the corresponding addition products.On the other hand, lithium diisopropylamide usually deprotonates the opposite carbon atom to generate enolates, R1CH(SiMe3)C(OLi)=CHR2, selectively, which yield another type of aldol product after removal of the silyl group.Thus, two types of aldols can be prepared regioselectively from common α-trimethylsilyl ketones.

A NEW METHOD FOR THE REGIO- AND STEREOSELECTIVE SYNTHESIS OF ALDOLS FROM α-BROMOKETONE AND CARBONYL COMPOUNDS BY USING METALLIC TIN

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

Regio- and Stereoselective Cross-aldol Reactions via Dialkylboryl Triflates

New borylating reagents, (Bu2BOTf and 9-BBNOTf), were prepared in high yields.The triflates reacted with enolizable ketones in the presence of tertiary amines to generate selectively one of the regioisomers of vinyloxyboranes by the choice of the reagents (the dialkylboryl triflates and tertiary amines) under mild reaction conditions.Vinyloxyboranes thus generated showed remarkable reactivity toward aldehydes to give only one regioisomer of the corresponding cross-aldols in good yields.High stereoselectivity was also observed in these reactions.