75463-67-1

Upstream product

• 106501-12-6 (E)-(3R,4S)-5-[1,3]Dithian-2-ylidene-4-methyl-1-phenyl-pent-1-en-3-ol 
• 104-55-2 3-phenyl-propenal 
• 131407-57-3 3-Methyl-4-oxo-6-phenyl-5-hexensaeure-methylester 
• 3152-68-9 (1E)-1-phenylpent-1-en-3-one 
• 84510-40-7 (3RS,4SR,1Z,5E)-4-hydroxy-1-methoxymethoxy-3-methyl-6-phenylhexa-1,5-diene 
• 1617-31-8 3-methylbut-3-enoic acid 
• 36525-03-8 trans-2-Phenylethenylmercuric chloride 
• 75463-66-0 (E)-3-methyl-4-oxo-6-phenyl-5-hexenoic acid 

Relevant academic research and scientific papers

Stereoselective Reduction of γ-Oxobutanoic Acids Using DIBAL-H and ZnCl2

A variety of γ-aromatic γ-ketobutanoic acids can be reduced selectively, under optimized conditions, by the use of DIBAL-H and ZnCl2 to provide the (RS,SR)-γ-aryl-γ-hydroxy-β-methylbutanoic acids.Further evidence has been gathered to support the hypothesis that the reaction proceeds by formation of a seven-membered ring complex with the aluminium or zinc atom bridging the ketone and carboxyl groups which preceeds the reduction step and that this templated reduction accounts for observed high diastereoselectivity.Also we have shown that some γ-aryl-γ-butyrolactones can be easily transformed via an oxidative cleavage of the aromatic ring to provide selective synthesis of either cis- or trans-tetrahydro-3-methyl-5-oxo-2-furancarboxylic acid derivatives.

Stereoselective Thermal Reactions between (E)-1-Alkoxymethoxybut-2-enyl(tributyl)stannanes and Aldehydes

(E)-1-Methoxymethoxybut-2-enyl(tributyl)stannane (6), readily available by the addition of tributylstannyl-lithium to crotonaldehyde and alkylation of the adduct using chloromethyl methyl ether, reacts on heating with aldehydes to give anti-4-hydroxy-3-methyl-cis-1,2-enol ethers.These on hydrolysis and oxidation provide trans-4,5-disubstituted butyrolactones.

Dichotomous Regiochemistry of Aldehyde and Ketone in the Reaction with Dithio-Substituted Crotyllithium

The crotyllithium compound 1 generated from (E)-2-(1-propen-1-yl)-1,3-dithiane reacted with an aldehyde to give γ-products in favor of the anti isomer.This regio- and diastereoselective reaction is applicable to syntheses of trans β,γ-disubstituted γ-lactones, including natural products of (+/-)-eldanolide and (+/-)-trans quercus lactone.The γ(1,2)-adducts obtained from the reaction of 1 and enals underwent alkoxy-Cope rearrangements on treatment with KH.The consequence is virtually complete α(1,4)-addition of crotyllithium 1 to α,β-unsaturated aldehydes.Crotyllithium 1 reacted with ketones at either the α- or the γ-site, depending on the nature of respective ketone.The regiochemistry is well interpreted by the hard and soft acids and bases principle, when the steric effect is a minor controlling factor.The effects of HMPA and reaction temperature on the regioselectivity were also evaluated.

MERCURY IN ORGANIC CHEMISTRY. 35. SYNTHESIS OF VINYLIC LACTONES FROM VINYLMERCURIALS AND ALKENOIC ACIDS VIA INTERMOLECULAR ?-ALLYLPALLADIUM DISPLACEMENT

The reaction of vinylmercuric chlorides, Li2PdCl4 and 3-butenoic or 4-pentenoic acids, followed by refluxing with K2CO3, affords high yields of the corresponding γ-alkenyl-γ-butyro- or δ-alkenyl-δ-valerolactones by an intramolecular ?-allylpalladium displacement process.

On The Use of E-1-Methoxymethoxybut-2-enyl(tri-n-butyl)stannane as a threo-Selective, Homo-enolate Equivalent

(E)-1-Methoxymethoxybut-2-enyl(tri-n-butyl)stannane, readily available by addition of tri-n-butylstannyl-lithium to crotonaldehyde, and protection of the alcohol so formed using chloromethyl methyl ether, reacts on heating with aromatic and aliphatic aldehydes to give threo-4-hydroxy-3-methyl-cis-1,2-enol ethers, hydrolysis and oxidation of which provides a stereoselective route to trans-4,5-disubstituted butyrolactones.