83565-88-2

Upstream product

• 4013-34-7 3-phenyl-2-oxabutane 
• 83565-80-4 ethyl 2-(trimethylsilyl)but-3-enoate 
• 16251-77-7 3-Phenylbutyraldehyde 
• 105-58-8 Diethyl carbonate 
• 867-13-0 diethoxyphosphoryl-acetic acid ethyl ester 
• 14371-10-9 (E)-3-phenylpropenal 
• 917-54-4 methyllithium 
• 585-71-7 (1-bromoethyl)benzne 
• 4157-77-1 (1-butoxyethyl)benzene 

Downstream Products

• 1338046-10-8 (E)-ethyl 5-phenylhex-4-enoate 

Relevant academic research and scientific papers

Remote Functionalization of α,β-Unsaturated Carbonyls by Multimetallic Sequential Catalysis

The remote functionalization of α,β-unsaturated carbonyls by an array of multimetallic sequential catalytic systems is described. The reactions are triggered by hydrometalation using [Pd-H] or [Ru-H] isomerization catalysts and driven by the formation of thermodynamically more stable 1,2-vinyl arenes. The Pd-catalyzed deconjugative isomerization was combined with a Cu-catalyzed β-borylation of the transiently generated styrenyl derivatives to deliver a range of products that would not be accessible with the use of a single catalyst. [Pd/Cu] catalytic systems were also identified for the highly enantioselective α-hydroboration and α-hydroamination of the styrenyl intermediates. Difunctionalization simultaneously at the benzylic and homobenzylic positions was achieved by combining the isomerization process with Sharpless asymmetric dihydroxylation (SAD) using [Pd/Os] or [Ru/Os] couples. Starting from a simple α,β-unsaturated ester, an isomerization/dihydroxylation/lactonization sequence gave access to a naturally occurring γ-butyrolactone in good yield, with excellent diastereo- and enantioselectivity.

Tandem Michael-Wittig-Horner reaction: Application to the synthesis of bisabolanes

Bisabolane derivatives have been synthesized from para-substituted cinnamaldehydes according to a tandem Michael - Wittig - Horner reaction. This sequence was applied to a short access to (+/-)-ar-turmerone.

Tandem Michael - Wittig - Horner reaction: One-pot synthesis of δ- substituted α,β-unsaturated carboxylic acid derivatives - application to a concise synthesis of (Z)- and (E)-ochtoden-1-al

A new tandem Michael-Wittig-Horner reaction has been developed to produce in high yields δ-substituted α,β-unsaturated esters, amides and lactones. The reaction has been successfully applied to a concise synthesis of (E)- and (Z)-ochtoden-1-als, component

Reactivity of substituted and unsubstituted diphenylphosphonium diylides towards carbonic acids derivatives

In order to further delimit the scope of application of diphenylphosphonium diylides, their reactivity towards carbonic acid derivatives was investigated. Non-stabilized diylides react with ethyl carbonate to give new monoylide intermediates which lead, by in situ Wittig reaction with carbonyl compounds, to the synthesis of α,β-unsaturated esters or acids the double bond being di- or trisubstituted. The reaction proceeds in mild conditions and with high E stereoselectivity. Stabilized diylides are inactive towards carbonates but semi-stabilized diylides react with ethyl carbonate leading to the synthesis of non-functionalized alkenes instead of the α,β-unsaturated esters or acids.

REGIOSELECTIVE COUPLING OF ALLYLIC ETHERS WITH ETHYL 2-TRIMETHYLSILYL-3-BUTENOATE

In the presence of TiCl4 the 4 position of the title silyl ester reacts with such electrophiles as allylic ethers or bromides carrying the leaving group on the secondary carbon without allylic rearrangement.