22472-79-3

Upstream product

• 89-82-7 pulegone 
• 555-31-7 aluminum isopropoxide 
• 67-63-0 isopropyl alcohol 
• 89-82-7 pulegone 
• 89-79-2 Isopulegol 

Downstream Products

• 23283-97-8 (+)-(1S,2R,5R)-isomenthol 
• 586-67-4 3,8-p-Menthadien 
• 24302-23-6 p-menth-3-en-8-ol 

Relevant academic research and scientific papers

Eco-friendly stereoselective reduction of α,β-unsaturated carbonyl compounds by Er(OTf)3/NaBH4 in 2-MeTHF

An operationally simple and environmentally benign catalytic procedure has been developed to selectively reduce different α,β-unsaturated ketones. The corresponding allylic alcohols are obtained with high chemo- and diastereoselectivity using Er(OTf)3 and NaBH4 in 2-MeTHF. This protocol reduces the amount of catalyst and NaBH4 needed, compared to classical procedures and the stages of extraction/purification are carried out in aqueous solutions avoiding the use of toxic solvents. Taking into account that Er(OTf)3 can be considered even less toxic than table salt and the 'greenness' of 2-MeTHF as a solvent, the system Er(OTf)3/2-MeTHF can be proposed as a cheap, efficient, and environmentally sustainable reduction system for the synthesis of allylic alcohols.

CuH-catalyzed enantioselective 1,2-reductions of α,β-unsaturated ketones

The first study on a general technology for arriving at valued nonracemic allylic alcohols using asymmetric ligand-accelerated catalysis by copper hydride is described.

Bioreduction of aldehydes and ketones using Manihot species

Biocatalysis constitutes an important tool in organic synthesis, especially for the preparation of chiral molecules of biological interest. A series of aliphatic and aromatic aldehydes and two ketones were reduced using plant cell preparations from Manihot esculenta and Manihot dulcis roots. The reduced products were typically obtained in excellent yields (80-96%), and with excellent enantiomeric excess (94-98%), except for vanillin. Esters, a nitrile, and an amide were also examined, but were not reduced. Preliminary conversion rate studies are reported. This is the first attempt to perform the biotransformation of carbonyl compounds using Manihot species.

Lipase-catalyzed resolution of p-menthan-3-ols monoterpenes: Preparation of the enantiomer-enriched forms of menthol, isopulegol, trans- and cis-piperitol, and cis-isopiperitenol

A study on the enzymic resolution of the most common p-menthan-3-ol monoterpene isomers is described. Enantioenriched alcohols 1, 5, 10, 11 and 12 are obtained by means of the lipase-mediated kinetic acetylation of the corresponding racemic materials. The stereochemical aspects of the enzymic process have been investigated. We found that the structural features of the starting p-menthan-3-ol as well as the kind of lipase used, impacted strongly on the enantioselectivity of the resolution. The potentialities of this approach for preparative purposes are discussed.

Method for producing 1-menthol

Provided is a method for the production of 1-menthol, which comprises hydrogenation of piperitenone with a transition metal complex of a specified optically active phosphine to produce pulegone, hydrogenation of the obtained pulegone with a ruthenium-phosphine-amine complex in the presence of base to obtain pulegol, and further hydrogenation of the pulegol with a transition metal catalyst.

Asymmetric hydrogenation of cyclic α,β-unsaturated ketones to chiral allylic alcohols

The Ru(II)-BINAP-1,2-diphenylethylenediamine combined catalyst system effects asymmetric hydrogenation of certain cyclic enones in 2-propanol containing KOH with a substrate/catalyst molar ratio of 250 to 2500. The hydrogenation occurs selectively at the C=O function with excellent enantio- or diastereoselectivity.

Aminoborohydrides. 2. Regiospecific reductions of α,β-unsaturated carbonyl compounds with lithium pyrrolidinoborohydride. A facile conversion of α,β-unsaturated aldehydes and ketones to the corresponding allylic alcohols in high purity

Lithium aminoborohydrides (LiABH3), obtained by the reaction of n-BuLi with amine-boranes, are powerful reducing agents for the reduction α,β-unsaturated aldehydes and ketones to the corresponding allylic alcohols. Thus, lithium pyrrolidinoborohydride (LiPyrrBH3) and reduces cinnamaldehyde and cyclohexenone to give exclusively cinnamyl alcohol and 2-cyclohexen-1-ol respectively. This 1,2-reduction appears to be general and ester groups are tolerated. The yield of allylic alcohols from this procedure is essentially quantitative.

Lanthanoids in Organic Synthesis. 6. The Reduction of α-Enones by Sodium Borohydride in the Presence of Lanthanoid Chlorides: Synthetic and Mechanistic Aspects

Lanthanoid chlorides (LnCl3) are efficient catalysts for the regioselective 1,2-reduction of α-enones by NaBH4 in methanol solution.Optimal conditions of this reaction have been determined.A mechanistic interpretation depicting the role of the Ln3+ ions is given.The major effect of Ln3+ is the catalysis of BH4- decomposition by the hydroxylic solvent to afford alkoxyborohydrides, which may be responsible for the observed regioselectivity.The stereoselectivity of the process is also modified by the presence of the Ln3+ ions, in that axial attack of cyclohexanone systems is enhanced.

ALKYL METAL ASYMMETRIC REDUCTION. 11. THE REACTION OF α,β-UNSATURATED KETONES WITH β-BRANCHED TRIALKYLALUMINIUM COMPOUNDS.

The reduction of a series of α,β-unsaturated ketones has been studied under various experimental conditions, by using β-branched trialkylalanes.Asymmetric induction phenomena are observed when optically active trialkylalanes are used.