96391-85-4

Upstream product

• 693-03-8 n-butyl magnesium bromide 
• 84519-63-1 (R,E)-4-phenyl-3-buten-2-yl acetate 
• 109-72-8 n-butyllithium 
• 81176-43-4 (S)-trans-4-phenyl-3-buten-2-ol 

Relevant academic research and scientific papers

Enantioselective synthesis of α-methyl carboxylic acids from readily available starting materials via chemoenzymatic dynamic kinetic resolution

An enantioselective method for the synthesis of α-methyl carboxylic acids starting from trans-cinnamaldehyde, a readily available and inexpensive compound, has been developed. Allylic alcohol 1 was obtained via a standard Grignard addition to trans-cinnamaldehyde. Dynamic kinetic resolution was applied to allylic alcohol 1 utilizing a ruthenium catalyst and either an (R)-selective lipase or an (S)-selective protease to provide the corresponding allylic esters in high yield and high ee. A copper-catalyzed allylic substitution was then applied to provide the corresponding alkenes with inversion of stereochemistry. Subsequent C-C double bond cleavage afforded pharmaceutically important α-methyl substituted carboxylic acids in high ee and overall yields of up to 76%.

Alkylation of Allylic Derivatives. 9. On the Stereochemistry of Alkylation of Acyclic Allylic Alcohols by the Murahashi Method

The stereochemistry of alkylation of optically active trans-α-methyl-γ-phenylallyl alcohol (3-OH) by the Murahashi procdeure has been investigated.Alkylation with n-butyllithium results in almost exclusive syn γ-alkylation.With methyllithium, syn γ-alkylation also predominates.The syn stereochemistry in this acyclic system is opposite from that observed earlier in cyclic systems.Mechanistic implications of this reversal of stereochemistry are discussed.