81286-81-9

Upstream product

• 62617-39-4 1,1-dimethoxy-2,2-dimethylpropane 
• 611-71-2 MANDELIC ACID 
• 630-19-3 pivalaldehyde 
• 147-85-3 L-proline 
• 17199-29-0 (S)-Mandelic acid 
• 78804-02-1 (+/-)-trimethylsilyl 2-<(trimethylsilyl)oxy>-2-phenylethanoate 

Downstream Products

• 495-40-9 propiophenone 

Relevant academic research and scientific papers

Convenient synthesis of O-functionalized mandelic acids via Lewis acid mediated transformation of 1,3-dioxolan-4-ones

An efficient method for the synthesis of O-substituted mandelic acids containing alkenyl, alkynyl, methoxycarbonyl, or phenacyl fragments via the Lewis acid-catalyzed reaction of 1,3-dioxolan-4-ones with different C-nucleophiles is proposed.

Practical synthesis of 2,5-disubstituted 1,3-dioxolane-4-ones and highly diastereoselective cis-2,5-disubstituted 1,3-dioxolane-4-ones from α-hydroxy acids catalyzed by N-triflylphosphoramide

N-triflylphosphoramide (NTPA) was found to be an efficient Br?nsted acid catalyst for the practical synthesis of 2,5-disubstituted 1,3-dioxolane-4-ones. Racemic and optically pure mandelic acid and lactic acid could be protected using several aldehydes in

A remarkable bismuth nitrate-catalyzed protection of carbonyl compounds

Bismuth nitrate has been found to be an outstanding catalyst for the protection of carbonyl compounds as acetal, ketal, mixed ketal and thioketal with an excellent yield.

A large-scale asymmetric synthesis of (S)-cyclohexylphenyl glycolic acid

A practical asymmetric synthesis of (S)-cyclohexylphenyl glycolic acid has been demonstrated at pilot scale. The key step is the asymmetric aldol reaction using the Seebach approach of self-replication of stereochemistry. (S)-Mandelic acid was converted i

A new highly diastereoselective synthesis of 2,5-disubstituted-1,3-dioxolan-4-ones from α-hydroxyacids

Reaction of α-hydroxyacids with acetals under weak acid catalysis gave the corresponding dioxolanones with a better diastereomeric ratio than the usual strong acid catalyzed synthesis from aldehydes.

α-ALKYLATION OF α-HETEROSUBSTITUTED CARBOXYLIC ACIDS WITHOUT RACEMIZATION; EPC-SYNTHESES OF TERTIARY ALCOHOLS AND THIOLS

α-Hydroxy- and α-mercapto-carboxylic acids are condensed with pivalaldehyde to give 2-t-butyl-5-substituted-1,3-dioxolanones or 1,3-oxathiolanones (2); the predominate cis-isomers are separeted by crystallization.The cis-disubstituted heterocycles 2 derived from lactic, mandelic and malic acid funish, after deprotonation with LDA, reaction with electrophiles such as alkyl halides, aldehydes and ketones, and hydrolysis α-branched α-hydroxy-carboxylic acids (3, 6, 8, 9, 10).These result from an overall substitution of the proton in the α-CO position with retention of configuration.The optically active carboxylic acids are α-alkylated without racemization and without employment of a chiral auxiliary ("self-reproduction of chirality", Scheme 1).The diastereoselectivities (ds) are generally >95percent (Table 1, 2, and 20-25).

OPTICAL ACTIVITY OF LACTONES AND LACTAMS-I; CONFORMATIONAL DEPENDENCE OF THE CIRCULAR DICHROISM OF 1,3-DIOXOLAN-4-ONES

Several optically active 1,3-dioxolan-4-ones were synthesized from corresponding α-hydroxy acids.The Cotton effect sign of these compounds can be explained by Weigans's sector rules.The existence of an equilibrium between envelope and planar conformations

Enantioselective Generation and Diastereoselective Reactions of Chiral Enolates Derived from α-Heterosubstituted Carboxylic Acids

Dioxolanones 7 and 8a and oxazolinones 9a derived from pivalaldehyde and lactic acid, mandelic acid, and proline, respectively, furnish chiral enolates of type 3 by deprotonation with LDA.Reactions of these enolates with alkyl halides, aldehydes, and keto