83071-79-8

Upstream product

• 87-69-4 L-Tartaric acid 
• 108-93-0 cyclohexanol 
• 621-13-6 dicyclohexyl trans-butenedioate 
• 133-37-9 DL-tartaric acid 

Downstream Products

• 283151-88-2 [3R,4R]-(+)-4-hydroxy-3-methyl-4-phenyl-2-butanone 
• 125354-83-8 (-)-syn-4-hydroxy-3-methyl-4-phenylbutan-2-one 
• 1026024-00-9 (4R,5R)-bis(cyclohexyloxycarbonyl)-2-chloro-1,3,2-dioxaphospholane 
• 133017-22-8 cyclohexyl glyoxalate 
• 133017-23-9 Dihydroxy-acetic acid cyclohexyl ester 
• 130678-48-7 Dicyclohexyl-(4R,5R)-2-<(2RS,6RS)-2,6,10-trimethylundecyl>-1,3-dioxolan-4,5-dicarboxylat 

Relevant academic research and scientific papers

2-Chloro-(4R,5R)-bis[(1R,2S,5R)-menth-1-yloxycarbonyl]-1,3, 2-dioxaphospholane: A practical chiral pool-derived reagent for determining enantiomeric purity of alcohols

(Chemical Equation Presented) 2-Chloro-(4R,5R)-bis[(1R,2S,5R)-menth-1- yloxycarbonyl)]-1,3,2-dioxaphospholane is a practical reagent for reliably determining enantiomeric purity of chiral alcohols via 31P NMR spectroscopy. The compound is available as a crystalline solid on a 20 g scale from PCl3 and bis[(1R,2S,5R)-menth-1-yl] tartrate. It is comparatively inert toward spontaneous hydrolysis under conventional laboratory conditions but undergoes quantitative substitution of alkoxide for chloride if treated with a chiral alcohol. Nonequivalent 31P NMR signals of diastereomeric 2-alkoxy-1,3,2-dioxophospholanes were dispersed by ～1.4-0.1 ppm. The associated integral ratios reflected enantiomeric purities of preweighted samples of (R)- and (S)-1-phenylethanol, (+)- and (-)-menthol, and a set of primary, secondary, and tertiary alcohols with a precision of ±0.4-1.0%.

Enantioselective distribution of amino-alcohols in a liquid-liquid two-phase system containing dialkyl L-tartrate and boric acid

Racemic amino-alcohols such as pindolol, propranolol, alprenolol and bucumolol enantiomers exhibited different distribution behaviors in a two-phase system consisting of a chloroform solution of didodecyl L-tartrate and an aqueous solution of boric acid. It seemed that a borate complex of the 1,2-diol group of the tartrate and the amino-alcohol was formed in the system. In the case of pindolol, one enantiomer was preferentially extracted into the organic phase (x 2.20) at equilibrium.

A Useful Synthesis of Chiral Glyoxylates

A convenient synthesis of the cyclohexyl, (1R,3R,4S)-3-p-methyl and (1S-endo)-2-bornyl glyoxylates, from the respective alcohols and other very available materials, as a model applicable to that of other chiral, sensitive glyoxylates, is described.

Structural Aspects of the Enantioselectivity of Tartrates with α-Amino-alcohol Salts. Part I. Crystal Structures of Eleven Tartaric-Acid Diesters

Enantioselective host-guest complexes of α-amino-alcohol salt with chiral tartaric-acid esters can not be crystallised up to now.To study structural aspects of their enantioselectivity, crystal structures of the components were determined.The structures of eleven diesters with myrnatol, borneol, menthol, neomenthol, and cis-4-(tert-butyl)cyclohexanol in different configurations showed a remarkable rigidity of the tartaric-acid conformation, partly because of intermolecular H-bonding between OH and C=O groups.The conformation of the tartaric-acid part in these diesters is the same as the one observed in optically active tartaric acid (torsion angle O=C-C-OH ca. 0 deg).The binding site for guest molecules is a parallelogram formed by two hydroxy and two carbonyl O-atoms, all lying on the same side of a mean molecular plane.There is one exception: the dimenthyl ester, which is the most enantioselective with a norephedrine guest, has one of the ester groups turned (torsion angle O=C-C-OH ca. 180 deg), forming a triangle of O-atoms and moving the bulky menthyl group to the vicinity of the binding site.

Catalytic Asymmetric Epoxidation and Kinetic Resolution: Modified Procedures Including in Situ Derivatization

The use of 3A or 4A molecular sieves ( zeoiltes ) substantially increases the scope of the titanium(IV)-catalyzed asymmetric epoxidation of primary allylic alcohols.Whereas without molecular sieves epoxidations employing only 5 to 10 mol percent Ti(O-i-Pr)4 generally led to low conversion or low enantioselectivity, in the presence of molecular sieves such reactions generally led to high conversion (>95percent) and high enantioselectivity (90-95percent ee).The epoxidations of 20 primary allylic alcohols are described.Especially noteworthy are the epoxidations of cinnamyl alcohol, 2-tetradecyl-2-propen-1-ol, allyl alcohol, and crotyl alcohol-compounds which heretofore had been considered difficult substrates for asymmetric epoxidation.In the case of allylic alcohol, the use of cumene hydroperoxide substantially increases both the reaction rate and the conversion, even in the absence of molecular sieves.In general, enantioselectivities are slightly depressed (by 1-5percent ee) relative to reactions employing 50-100 mol percent Ti(O-i-Pr)4.The epoxidation of low molecular weight allylic alcohols is especially facilitated and, in conjuction with in situ derivatization, provides for the synthesis of many epoxy alcohol synthons which were previously difficult to obtain.The kinetic resolution of four secondary allylic alcohols with 10 mol percent Ti(O-i-Pr)4 is also described.The role of molecular sieves in the reaction and the effects of variation in reaction stoichiometry, oxidant, and tartrate are discussed.