1502-80-3

Upstream product

• 56907-39-2 rac-(2R,3S)-3-phenylbutan-2-ol 
• 32123-84-5 3-phenylbut-3-en-2-one 
• 79120-96-0 (R)-(-)-3-phenylbutan-2-one 
• 591-51-5 phenyllithium 
• 925669-95-0 2,3-cis-epoxybutane 
• 766-90-5 cis-1-phenyl-1-propylene 
• 74-88-4 methyl iodide 
• 135-98-8 sec-Butylbenzene 
• 21490-63-1 2,3-trans-epoxybutane 
• 1123-85-9 (RS)-2-phenyl-1-propanol 
• 768-00-3 (E)-2-phenyl-2-butene 
• 31508-44-8 2-phenylpropionic acid methyl ester 
• 34713-70-7 2-Phenylpropanal 
• 492-37-5 hydratropic acid 

Downstream Products

• 1499-67-8 (2S,3R)-3-cyclohexyl-butan-2-ol 
• 42879-20-9 (2S,3R)-3-phenylbutan-2-yl acetate 

Relevant academic research and scientific papers

Asymmetric Reduction of Carbon-Carbon Double Bonds of Conjugated Enones with Fermenting Bakers' yeast

Bakers' yeast reduction of α-substituted or β,β-disubstituted α,β-unsaturated ketones gave saturated chiral ketones with excellent optical purity, while the β,β-disubstituted derivatives remains intact.

Highly enantioselective arylation of symmetrical epoxides with phenyllithium promoted by chiral Schiff bases and salens

Cyclohexene oxide and cyclopentene oxide react with phenyllithium to give highly optically active trans-2-phenyl-1-cyclohexanol and -cyclopentanol in the presence of a small amount of chiral Schiff bases and salens.

Monoisopinocampheylborane: An Excellent Chiral Hydroborating Agent for Phenyl-Substituted Tertiary Olefins. Synthesis of Alcohols Approaching 100percent Enantiomeric Excess

Monoisopinocampheylborane (IPCBH2), a less hindered chiral hydroborating agent, is highly effective for the hydroboration of phenyl-substituted tertiary olefins, such as 1-phenyl-1-cyclopentene, 1-phenyl-1-cyclohexene, (E)- and (Z)-2-phenyl-2-butenes, and

Enantioselective Copper-Catalyzed Methylboration of Alkenes

An enantioselective Cu-catalyzed borylative cross-coupling reaction of alkenes, bis(pinacolato)diboron (B2(pin)2), and methyl iodide is reported. Alkenes including styrenes, β-substituted styrenes, and challenging aliphatic olefins were smoothly transferred to the desired methylboration products with excellent diastereoselectivities (dr up to >99:1) and enantioselectivities (er up to 99:1). The utility of this process was demonstrated by the synthesis of naproxen and formal synthesis of two natural products.

Dynamic Reductive Kinetic Resolution of Benzyl Ketones using Alcohol Dehydrogenases and Anion Exchange Resins

Dynamic reductive kinetic resolutions of racemic 3-arylalkanones have been performed by the proper combination of an alcohol dehydrogenase and a basic anionic resin. The best results were found for the bioreduction with the alcohol dehydrogenase type A from Rhodococcus ruber DSM 44541 overexpressed in Escherichia coli (E. coli/ADH-A) and the commercially available evo-1.1.200, while the Amberlite IRA-440 C and the DOWEX-MWA-1 resins allowed efficient in situ racemizations. Reaction conditions were optimized in terms of enzyme source and loading, type and amount of resin, pH, temperature and reaction times, obtaining a series of (R,R)-substituted propan-2-ols with good conversions and both diastereoselectivity and stereoselectivity. As a proof of concept, the subsequent intramolecular cyclization of a selected propan-2-ol substrate afforded a valuable isochroman heterocycle without any loss of the optical purity.

Tandem hydroboration/reduction of trisubstituted β,γ-unsaturated esters for the asymmetric synthesis of chiral 1,3-diols

Treatment of a range of trisubstituted β,γ-unsaturated esters with 2 equiv of (-)-monoisopinocampheylborane results in hydroboration of their alkene functionalities and reduction of their ester groups to afford chiral 1,3-diols containing two new vicinal

Screening on the use of Kluyveromyces marxianus CBS 6556 growing cells as enantioselective biocatalysts for ketone reductions

The versatility of Kluyveromyces marxianus CBS 6556 growing cells in the enantioselective reduction of ketone functionalities to the corresponding alcohols was exploited. In particular, methyl ketones were reduced to (S)-alcohols with ees of up to 96%. Longer chain alkyl ketones afforded, under the same experimental condition, (R)-alcohols with an ee of up to 84%. Interestingly, carbon-carbon double and the triple bonds can also be reduced in the presence of Kluyveromyces marxianus CBS 6556 yeast. A cyclic ketone, such as 2-tetralone, was also quantitatively reduced to its corresponding (S)-alcohol with ee = 76%.

Remote stereocontrol by sulfinyl groups: Reduction of δ- ketosulfoxides

(Chemical Equation Presented) The reduction of δ-ketosulfoxides constitutes the first evidence of the efficiency of the sulfinyl group to control the stereoselectivity of 1,5-asymmetric induction processes. The use of DIBAL/Yb(OTf)3 or L-Selectride as the reducing agents provides δ-hydroxysulfoxides with the opposite configuration at the hydroxylic carbon in a highly stereoselective way.

Samarium diiodide-promoted diiodomethylation of carbonyl compounds with iodoform. Synthetic applications of diiodoalcohols

A rapid and effective diiodomethylation of carbonyl compounds using SmI2 and iodoform is described. Transformations of the obtained diiodoalcohols 2 into α-iodoaldehydes 5 and α-hydroxyacids 6 is also reported.

Enantiopreference of Lipase from Pseudomonas cepacia toward Primary Alcohols

We propose an empirical rule that predicts which enantiomer of primary alcohol reacts faster in reactions catalyzed by lipase from Pseudomonas cepacia (PCL).This rule, based on the size of the substituents at the stereocenter, shows an 89percent reliability (correct for 54 of 61 examples).This rule is not reliable for primary alcohols that have an oxygen atom attached to the stereocenter; we excluded these alcohols from the tally above.Surprisingly, the sense of enantiopreference of PCL toward primary alcohols is opposit to its enantiopreference toward secondary alcohols.That is, the OH of secondary alcohols and the CH2OH of primary alcohols point in opposite directions.We suggest, however, that this opposite orientation does not imply a different position of the substituents in the active site of the lipase.Instead, PCL accommodates the extra CH2 in primary alcohols as a kink between the stereocenter and the oxygen which allows a similar position of the alcohols by increasing the diffrence in the size of the substituents but did not find a consistent increase in enantioselectivity.We suggest that high enantioselectivity toward primary alcohols requires not only a significant difference in the size of the substituents, but also control of the conformation along the C(1)-C(2) bond.