1472-07-7

Usage

InChI:InChI=1/C11H14O2/c1-9(8-11(12)13-2)10-6-4-3-5-7-10/h3-7,9H,8H2,1-2H3/t9-/m1/s1

Upstream product

• 186581-53-3 diazomethane 
• 25145-43-1 (2S)-2-phenylpropionyl chloride 
• 126434-57-9 (-)-(R)-Methyl 3-(mesyloxy)butanoate 
• 71-43-2 benzene 
• 3461-39-0 3-phenyl-butyric acid methyl ester 
• 623-43-8 crotonic acid methyl ester 
• 2996-92-1 phenyl trimethylsiloxane 
• 214759-91-8 N-methoxy-N-methyl-3-phenylbutanamide 
• 67-56-1 methanol 
• 772-14-5 (R)-3-phenylbutyric acid 
• 68204-17-1 3-phenylbut-2-enoyl chloride 
• 160538-63-6 (4R)-4-phenyl-3-<(3R)-3-phenylbutyryl>oxazolidin-2-one 
• 98-86-2 acetophenone 
• 221878-52-0 (+/-)-3-phenylbutyric acid vinyl ester 

Downstream Products

• 772-14-5 (R)-3-phenylbutyric acid 
• 42307-58-4 3-phenylbutanal 
• 135-98-8 (2R)-sec-butylbenzene 
• 221878-55-3 (R)-(-)-vinyl 3-phenylbutanoate 
• 2031-46-1 (R)-3-phenylbutanol 

Relevant academic research and scientific papers

An efficient preparative scale resolution of 3-phenylbutyric acid by lipase from Burkholderia cepacia (Chirazyme L1)

Lipase from Burkholderia cepacia (Chirazyme L1) catalysed the highly enantioselective hydrolysis of racemic methyl 3-phenylbutyrate to afford (R)- (-)-methyl 3-phenylbutyrate of >98% ee (E>50). The resolution was performed at 150 g scale yielding 68.7 g of (R)-(-)-methyl 3-phenylbutyrate (>98% ee, 92% yield on enantiomer) and (S)-(+)-3-phenylbutyric acid of 89% ee.

Ni-catalyzed direct alcoholysis of N-acylpyrrole-type tertiary amides under mild conditions

N-Acylpyrrole-type amides are a class of versatile building blocks in asymmetric synthesis. We report that by employing Ni(COD)2/2,2′-bipyridine (5 mol%) catalytic system, the direct, catalytic alcoholysis of N-acylpyrrole-type aromatic and aliphatic amides with both primary and secondary alcohols can be achieved efficiently under very mild conditions (rt, 1 h) even at gram scale. By increasing the catalyst loading to 10 mol%, prolonging reaction time (18 h), and/or elevating reaction temperature to 50 °C/80 °C, the reaction could be extended to both complex and hindered N-acylpyrroles as well as to N-acylpyrazoles, Nacylindoles, and to other (functionalized) primary and secondary alcohols. In all cases, only 1.5 equiv. of alcohol were used. The value of the method has been demonstrated by the racemization-free, catalytic alcoholysis of chiral amides yielded from other asymmetric methodologies.

Chiral auxiliary recycling in continuous flow: Automated recovery and reuse of Oppolzer's sultam

The telescoping of a three-stage, chiral auxiliary-mediated transformation in flow is described, including continuous separation of the product and auxiliary. The auxiliary can either be collected for later reuse, or directly fed back to the beginning of the process for recycling in real time, enabling each molecule of auxiliary to make multiple equivalents of chiral product and thus minimizing the step- and atom-economy issues associated with auxiliary-mediated synthesis. This concept is demonstrated for the asymmetric hydrogenation of olefins using Oppolzer's sultam, shortening the total reaction time >100 fold compared to batch, and demonstrating formal sub-stoichiometric auxiliary loading with respect to the process by automating auxiliary recycling within a closed loop.

Direct Lewis Acid Catalyzed Conversion of Enantioenriched N-Acyloxazolidinones to Chiral Esters, Amides, and Acids

The identification of Yb(OTf)3 through a multivariable high-throughput experimentation strategy has enabled a unified protocol for the direct conversion of enantioenriched N-acyloxazolidinones to the corresponding chiral esters, amides, and carboxylic acids. This straightforward and catalytic method has shown remarkable chemoselectivity for substitution at the acyclic N-acyl carbonyl for a diverse array of N-acyloxazolidinone substrates. The ionic radius of the Lewis acid catalyst was demonstrated as a key driver of catalyst performance that led to the identification of a robust and scalable esterification of a pharmaceutical intermediate using catalytic Y(OTf)3.

Ni-Catalyzed chemoselective alcoholysis of: N -acyloxazolidinones

Although N-acyloxazolidinone-based (catalytic) asymmetric synthetic methodologies occupy an important position in modern organic synthesis, the catalytic cleavage of a chiral auxiliary remains underdeveloped. We report the Ni(cod)2/bipyr.-catalyzed alcoholysis of N-acyloxazolidinones to deliver esters. The reaction is broad in scope for both N-acyloxazolidinone substrates and alcohol nucleophiles, and displays good functional group tolerance and excellent chemoselectivity. A gram-scale methanolysis allowed the enantioselective synthesis of the C22-C26 segment of a close analogue of the potent immunosuppressant agent FK506.

Rhodium-Catalyzed Asymmetric Hydrogenation of α,β-Unsaturated Carbonyl Compounds via Thiourea Hydrogen Bonding

The strategy of secondary interaction enables enantioselectivity for homogeneous hydrogenation. By introducing hydrogen bonding of substrates with thiourea from the ligand, α,β-unsaturated carbonyl compounds, such as amides and esters, are hydrogenated wi

Asymmetric NaBH4 1,4-reduction of C3-disubstituted 2-propenoates catalyzed by a diamidine cobalt complex

A new Co complex of a unique diamidine ligand catalyzes asymmetric NaBH4 reduction of C3-disubstituted (E)- and (Z)-2-propenoates, including C3-oxygen- and nitrogen-substituted substrates with high enantioselectivity. Analysis by X-ray diffract

Expanded scope of the asymmetric hydrogenation of minimally functionalized olefins catalyzed by iridium complexes with phosphite-thiazoline ligands

We have replaced the oxazoline group with a thiazoline moiety in one of the most successful of the phosphite-oxazoline ligand families for the Ir-catalyzed hydrogenation of minimally functionalized olefins. A small but structurally important library of Ir phosphite-thiazoline precatalysts (Ir-L1-L2a-e) has been developed by changing the substituents/configurations at the biaryl phosphite group. We found that the replacement of the oxazoline with a thiazoline moiety in the ligand design is beneficial in terms of substrate scope.

Chiral ferrocenyl phosphine-phosphoramidite ligands for Cu-catalyzed asymmetric conjugate reduction of α,β-unsaturated esters

Unsymmetrical hybrid chiral ferrocenyl phosphine-phosphoramidite ligands have been applied for the first time in the Cu-catalyzed asymmetric 1,4-reduction of β-aryl substituted α,β-unsaturated esters. The results show that the ligand bearing (Sc/sub

Pyranoside phosphite-oxazoline ligands for the highly versatile and enantioselective Ir-catalyzed hydrogenation of minimally functionalized olefins. A combined theoretical and experimental study

A modular set of phosphite-oxazoline (P,N) ligands has been applied to the title reaction. Excellent ligands have been identified for a range of substrates, including previously challenging terminally disubstituted olefins, where we now have reached enantioselectivities of 99% for a range of substrates. The selectivity is best for minimally functionalized substrates with at least a moderate size difference between geminal groups. A DFT study has allowed identification of the preferred pathway. Computational prediction of enantioselectivities gave very good accuracy.