115346-55-9

Upstream product

• 125303-61-9 [(2S,3S)-3-phenethyloxiran-2-yl]methanol 
• 53376-62-8 ethyl 3-hydroxy-5-phenylpentanoate 
• 115346-89-9 5-phenyl-1,3-bis(trimethylsiloxy)pentane 
• 104-53-0 3-phenyl-propionaldehyde 
• 588731-94-6 (2E,5S)-5-hydroxy-7-phenyl-2-heptenoic acid ethyl ester 
• 760188-98-5 (S)-3-Hydroxy-1-[(R)-4-(1-methyl-1-triethylsilanyloxy-ethyl)-2-thioxo-thiazolidin-3-yl]-5-phenyl-pentan-1-one 
• 212615-52-6 (2R,4S)-2-phenyl-4-(2-phenylethyl)-1,3-dioxane 
• 115346-74-2 (2S,6R,7S,10R)-7-Isopropyl-10-methyl-2-phenethyl-1,5-dioxa-spiro[5.5]undecane 
• 768-56-9 4-Phenylbut-1-ene 
• 1380225-15-9 C₁₄H₁₇NO 
• 133271-09-7 C₁₁H₁₄O₂ 
• 115404-97-2 5-phenyl-pentane-1,3-diol 

Downstream Products

• 125303-62-0 Toluene-4-sulfonic acid (S)-3-hydroxy-5-phenyl-pentyl ester 
• 115346-56-0 (S)-5-phenyl-1,3-pentanediyl diacetate 
• 78571-82-1 (R)-α-ethylbenzenepropanol acetate 
• 105836-17-7 (R)-1-phenyl-3-pentanol 

Relevant academic research and scientific papers

Asymmetric Palladium-Catalyzed Oxycarbonylation of Terminal Alkenes: Efficient Access to β-Hydroxy Alkylcarboxylic Acids

A novel PdII-catalyzed enantioselective oxycarbonylation of alkenes has been established. The ligand with an ethyl group at the C-6 position of Pyox plays a significant role in the intermolecular oxypalladation process, leading to high reactivity and excellent enantioselective control. Compared to the conventional methods, the reaction itself features alkenes as easily prepared starting materials, mild and operationally simple reaction conditions, and insensitivities to air and water. Moreover, this method allows for broad alkene substrate scope, excellent regio- and enantioselectivities, scalabilities and a wide array of applications, and provides a useful route for the convenient and straightforward synthesis of chiral β-hydroxy alkylcarboxylic acids/esters.

Lewis base catalyzed enantioselective additions of an N-silyl vinylketene imine

Outside the limits: In the title reaction the nucleophile 1 represents a synthetic equivalent of nucleophilic allylic nitriles and addresses some of the current limitations associated with reactions of allylic nitrile anions. Unsaturated nitriles containi

Palladium-catalyzed synthesis of enantiomerically pure α-substituted allylboronic esters and their addition to aldehydes

Tartrate-derived boronic esters 2 can be subjected to palladium-catalyzed carbonyl allylations with SnCl2 to obtain enantiomerically pure α-substituted allylboronic esters 8 and 9. The reaction proceeds regioselectively and with high, simple diastereoselectivity to form anti-products. Their addition to aldehydes yields enantiomerically enriched homoallylic alcohols 17 and 18, respectively. Synthesis, characterization, and a mechanistic rational is presented here.

Diastereo- and enantiomerically pure allylboronates: Their synthesis and scope

Allylboronates are highly attractive reagents for allyl additions. Enantiomerically pure, stable reagents with a stereogenic centre in a-position to boron are especially versatile, albeit often difficult to synthesize. Starting from boron-containing allyl alcohols 6 and 7, which are discussed in detail herein, a set of reagents were obtained via [3,3]-sigmatropic rearrangements and consecutive transformations in the side chain. The configurations could be established first by chemical correlation, but also by X-ray crystallography (16, 18, 34, and 39). Allyl additions were performed resulting in the formation of predominantly (Z)-configured homoallylic alcohols (31, 43-45) with high enantiomeric excess. Detailed investigations on the matched-mismatched interaction between the reagents 15/16 (and ent-15/ent-16, respectively) and isopropylidene glyceraldehyde 42 d are presented.

Enzymatic kinetic resolution of racemic 4-tetrahydropyranols by Candida rugosa lipase

Enzymatic kinetic resolution of (±)-hydroxytetrahydropyrans has been achieved for the first time by means of lipase-mediated transesterification to afford optically active (2S,4R)-tetrahydropyranyl acetates and (2R,4S)-tetrahydropyranols in excellent yiel

Lewis base activation of Lewis acids: Catalytic, enantioselective vinylogous aldol addition reactions

(Chemical Equation Presented) The generality of Lewis base catalyzed, Lewis acid mediated, enantioselective vinylogous aldol addition reactions has been investigated. The combination of silicon tetrachloride and chiral phosphoramides is a competent catalyst for highly selective additions of a variety of α,β-unsaturated ketone-, 1,3-diketone-, and α,β- unsaturated amide-derived dienolates to aldehydes. These reactions provided high levels of γ-site selectivity for a variety of substitution patterns on the dienyl unit. Both ketone- and morpholine amide-derived dienol ethers afforded high enantio- and diastereoselectivity in the addition to conjugated aldehydes. Although α,β-unsaturated ketone-derived dienolate did not react with aliphatic aldehydes, α,β-unsaturated amide-derived dienolates underwent addition at reasonable rates affording high yields of vinylogous aldol product. The enantioselectivities achieved with the morpholine derived-dienolate in the addition to aliphatic aldehydes was the highest afforded to date with the silicon tetrachloride-chiral phosphoramide system. Furthermore, the ability to cleanly convert the morpholine amide to a methyl ketone was demonstrated.

Lewis base activation of Lewis acids. Vinylogous aldol addition reactions of conjugated N,O-silyl ketene acetals to aldehydes

N,O-Silyl dienyl ketene acetals derived from unsaturated morpholine amides have been developed as highly useful reagents for vinylogous aldol addition reactions. In the presence of SiCl4 and the catalytic action of chiral phosphoramide (R,R)-3,

Lewis base activation of Lewis acids: Catalytic, enantioselective addition of silyl ketene acetals to aldehydes

The concept of Lewis base activation of Lewis acids has been reduced to practice for catalysis of the aldol reaction of silyl ketene acetals and silyl dienol ethers with aldehydes. The weakly acidic species, silicon tetrachloride (SiCl4), can b

Synthesis of a new N-acetyl thiazolidinethione reagent and its application to a highly selective asymmetric acetate aldol reaction

(Chemical Equation Presented) A new N-acetyl thiazolidinethione reagent, which undergoes highly diastereoselective aldol reactions upon enolization with dichlorophenylborane and (-)-sparteine and subsequent treatment with a variety of aldehydes, is descri

Inter- and intramolecular differentiation of enantiotopic dioxane acetals through oxazaborolidinone-mediated enantioselective ring-cleavage reaction: Kinetic resolution of racemic 1,3-alkanediols and asymmetric desymmetrization of meso-1,3-polyols

Acetals derived from racemic 1,3-alkanediols undergo kinetic resolution in chiral oxazaborolidinonemediated ring-cleavage reaction with nucleophiles such as enol silanes and allylic silanes. Enantioselectivity of the reaction is affected by nucleophiles, the N-sulfonyl groups of oxazaborolidinones, and the substituents attached to the acetal carbon. For disubstituted acetals rac-1 and for trisubstituted acetal rac-2, derived from syn-2,4-dimethyl-1,3-pentanediol, satisfactory enantioselectivity is obtained by using methallylsilane 7b,c as a nucleophile in combination with N-mesyloxazaborolidinone 4a. On the other hand, enantioselective reaction of trisubstituted acetal rac-3b, derived from anti-2,4-dimethyl-1,3-pentanediol, is realized by using silyl ketene acetal 5e in combination with N-tosyloxazaborolidinone 4b. The reaction conditions optimized for the kinetic resolution, or enantiomer differentiating reaction, of the racemic acetals are successfully applied to asymmetric desymmetrization of meso-1,3-polyols through intramolecular differentiation of the enantiotopic acetal moieties of the bis-acetal derivatives. The utility of the ring-cleavage reaction as a method for enantioselective terminal differentiation of prochiral polyols is demonstrated in convergent asymmetric synthesis of pentol derivative 35 corresponding to the C(19)-C(27) ansachain of rifamycin S.