54541-41-2

Upstream product

• 40474-22-4 cis/trans-2-Methyl-2-phenyl-1-cyclopropancarbonsaeure-methylester 
• 57956-39-5 3-hydroxy-2-methyl-3-phenylbutyric acid methyl ester 
• 3461-39-0 3-phenyl-butyric acid methyl ester 
• 74-88-4 methyl iodide 
• 53153-95-0 α,β-dimethyl-β-phenylpropionitrile 
• 19731-91-0 α-methyl-β-phenylbutyric acid 
• 100-42-5 styrene 
• 34880-70-1 [1-methoxyprop-1-enyloxy]trimethylsilane 
• 14367-28-3 methyl (2E)-2-methyl-3-phenylbut-2-enoate 
• 141-78-6 ethyl acetate 
• 100-58-3 phenylmagnesium bromide 
• 28557-00-8 phenylzinc chloride 

Downstream Products

• 19731-91-0 α-methyl-β-phenylbutyric acid 
• 130292-29-4 α-methyl-β-phenylbutyryl chloride 
• 22661-04-7 (2SR,3SR)-2-methyl-3-phenylbutan-1-ol 
• 22661-04-7 (2RS,3SR)-2-methyl-3-phenylbutan-1-ol 

Relevant academic research and scientific papers

Metalated nitriles: Internal 1,2-asymmetric induction

(Chemical Equation Presented) Steric screening: In alkylations of metalated nitriles containing vicinal methyl groups and a trisubstituted C=C bond, the butene moiety screens electrophilic attack from one diastereotopic face as the quaternary stereocenter

Divergent Synthetic Access to E- and Z-Stereodefined All-Carbon-Substituted Olefin Scaffolds: Application to Parallel Synthesis of (E)- and (Z)-Tamoxifens

A highly substrate-general synthesis of all-carbon-substituted E- and Z-stereodefined olefins is performed. The method comprises two sets of parallel and stereocomplementary preparations of (E)- and (Z)-α,β-unsaturated esters involving two robust and distinctive reactions: 1) stereocomplementary enol tosylations using readily available TsCl/diamine/(LiCl) base reagents, and 2) stereoretentive Negishi cross-coupling using the catalysts [Pd(dppe)Cl2] (for E) and [Pd(dppb)Cl2] (for Z). The present parallel approach is categorized as both type I (convergent approach: 16 examples, 56–87 % yield) and type II (divergent approach: 18 examples, 70–95 % yield). The obtained (E)- and (Z)-α,β-unsaturated ester scaffolds are successfully transformed into various E- and Z-stereodefined known and novel olefins (8×2 derivatization arrays). As a demonstration, application to the parallel synthesis of both (E)- and (Z)-tamoxifens, a representative motif of all-carbon-substituted olefins, is accomplished in a total of eight steps with an overall yield of 58 % (average 93 %) and 57 % (average 93 %), respectively.

Regioselective carboindation of simple alkenes with indium tribromide and ketene silyl acetals

(Equation Presented). The regioselective carboindation of simple alkenes with indium tribromide and ketene silyl acetals was accomplished. Various alkenes such as ethylene, 1-alkenes, and cyclic alkenes were applicable for this reaction system. The alkyli

Raising the ceiling of diastereoselectivity in hydrogen transfer on acyclic radicals

We report here that the monodentate complexation of Me2AlCl to an ester group significantly enhances the selectivity of hydrogen transfer on acyclic radicals flanked by both an ester functionality and a stereogenic center, leading to C-2,C-3-an

Metalated nitriles: Internal 1,2-asymmetric induction

(Chemical Equation Presented) Alkylations of conformationally constrained acyclic nitriles containing vicinal dimethyl groups and an adjacent phenyl group or trisubstituted alkene are exceptionally diastereoselective. Probing the alkylation stereoselectivity with a series of C- and N-metalated nitriles implicates a reactive conformation in which an sp2-hybridized substituent projects over the metalated nitrile to avoid allylic strain. Steric screening thereby directs the electrophilic attack to the face of the metalated nitrile opposite the projecting substituent. Excellent stereoselectively is maintained in a diverse range of alkylations that efficiently install quaternary centers, even with isopropyliodide in which a contiguous array of tertiary-quaternary-tertiary stereocenters is created! Screening the conformational requirements with a series of acyclic nitriles and esters reveals the key structural requirements for high selectivity while providing a robust, predictive model that accounts for comparable ester alkylations affording the opposite diastereomer! The intensive survey of metalated nitrile alkylations identifies the key structural features required for high 1,2-asymmetric induction, addresses the long-standing challenge of asymmetric alkylations with acylic metalated nitriles, and provides a versatile method for installing hindered quaternary centers with excellent stereocontrol.

The Use of Lewis Acids in Radical Chemistry. Chelation-Controlled Radical Reductions of Substituted α-Bromo-β-alkoxy Esters and Chelation-Controlled Radical Addition Reactions

The radical reduction of a series of α-bromo-β-alkoxy esters under chelation-controlled conditions is reported. Proceeding with high stereoselectivity in the presence of MgBr2middot;OEt2, reductions give access to syn products. Syste

Convenient Synthetic Sequence for the Preparation of Indanones

A convenient and general methods is reported for the synthesis of indanones from aryl ketones or aldehydes.

SELECTIVE REDUCTION OF DIARYL OR ARYL ALKYL ALCOHOLS IN THE PRESENCE OF PRIMARY HYDROXYL OR ESTER GROUPS BY ETHERATED BORON TRIFLUORIDE-TRIETHYLSILANE SYSTEM

Diaryl or alkyl aryl carbinols bearing a second reducible functional group (such as hydroxyl or ester) are selectively deoxygenated in high yields by the action of etherated boron trifluoride and triethyl silane reducing system.

Rate and Regioselectivity of Hydrogenolysis of Some Phenyl-Substituted Cyclopropanes

Several phenyl-substituted cyclopropane derivatives were investigated regarding rate and regiochemistry of their hydrogenolysis.The following reactivity sequence has been established: 1 2 4 7 9.Substituent effects are discussed and compared to those reported for monoactivated cyclopropanes.