5056-00-8

Upstream product

• 15356-60-2 (1S,2R,5S)-(+)-menthol 
• 5055-99-2 (+)-(1S,2S,5S)-carvomenthyl tosylate 
• 151-50-8 potassium cyanide 
• 99-87-6 4-methylisopropylbenzene 
• 491-07-6 isomenthone 
• 75-24-1 trimethylaluminum 
• 73316-48-0 Acetic acid (1S,6R)-6-isopropyl-cyclohex-2-enyl ester 
• 83670-70-6 Acetic acid (1S,4R)-4-isopropyl-cyclohex-2-enyl ester 
• 917-64-6 methyl magnesium iodide 
• 554-61-0 3,7,7-trimethylbicyclo[4.1.0]hept-2-ene 
• 491-04-3 trans-6-isopropyl-3-methylcyclohex-2-en-1-ol 
• 63296-63-9 cis-(+/-)-(1R,6SR)-6-isopropyl-2-cyclohexen-1-ol 

Downstream Products

• 3804-01-1 (1RS,2SR,3SR,4RS)-p-menthane-2,3-diol 
• 3804-01-1 (1RS,2RS,3RS,4RS)-p-menthane-2,3-diol 
• 3804-01-1 (1RS,2SR,3RS,4RS)-p-menthane-2,3-diol 

Relevant academic research and scientific papers

M -C2B10H11HgCl/AgOTf-Catalyzed Reaction for Reductive Deoxygenation

A m -C2B10H11HgCl/AgOTf-catalyzed reaction of allyl silyl ethers with N -Boc- N ′-tosylhydrazine has been developed. Under mild conditions, the resulting allyl hydrazine products were transformed into naked alkenes in good yield. Furthermore, the used m -C2B10H11HgCl could be recovered quantitatively.

Synthesis and sensory studies of umami-active scaffolds

The class of 2-isopropyl-5-methylbicyclo[4.1.0]heptane-7-carboxamides, 1-4, has been identified as potent umami-tasting molecules. A scalable synthesis of this challenging scaffold and new sensory insights will be presented. Interestingly, the umami chara

Radical chain reduction of alkylboron compounds with catechols

The conversion of alkylboranes to the corresponding alkanes is classically per-formed via protonolysis of alkylboranes. This simple reaction requires the use of severe reaction conditions, that is, treatment with a carboxylic acid at high temperature (>150 °C). We report here a mild radical procedure for the transformation of organoboranes to alkanes. 4-tert-Butylcatechol, a well-established radical inhibitor and antioxidant, is acting as a source of hydrogen atoms. An efficient chain reaction is observed due to the exceptional reactivity of phenoxyl radicals toward alkylboranes. The reaction has been applied to a wide range of organoboron derivatives such as B- alkylcatecholboranes, trialkylboranes, pinacolboronates, and alkylboronic acids. Furthermore, the so far elusive rate constants for the hydrogen transfer between secondary alkyl radical and catechol derivatives have been experimentally determined. Interestingly, they are less than 1 order of magnitude slower than that of tin hydride at 80 °C, making catechols particularly attractive for a wide range of transformations involving C-C bond formation.

O-DPPB-directed copper-mediated and -Catalyzed allylic substitution with grignard reagents

The ortho-diphenylphosphanylbenzoyl (o-DPPB) group was explored as a directing leaving group in copper-mediated and copper-catalyzed allylic substitution with Grignard reagents. Complete control of chemo-, regio- and stereoselectivity with complete syn-1,3-chirality transfer was observed as a result of the directed nature of the reaction. No excess of or ganometallic reagent is required and the directing group can be recovered quantitatively. Coordination studies in the solid state and in solution have shown that two substrates are bound via the phosphine function of the directing group at copper. Dynamic NMR experiments in solution are in agreement with a ligand-exchange process at copper, a prerequisite for the development of a substoichiometric process.

Copper-Mediated and -Catalyzed o-DPPB-Directed Allylic Substitution

Complete control of chemo-, regio- and stereoselectivity in the course of copper-catalyzed and -mediated allylic substitution could be obtained with me ortho-diphenylphosphanyl (o-DPPB) function as a reagent-directing leaving group. Complete chirality transfer by way of a syn-addition process has been achieved for cyclic and acyclic systems. Readily available Grignard reagents may be employed as nucleophiles and the directing o-DPPB group can be recovered quantitatively. The reaction requires neither cooling nor an excess of organometallic reagent.

Anomalous hydroalumination of methyl nopol ether with a LiAlH4-3AlBr3 system

Hydroalumination of methyl nopol ether with LiAlH4-3AlBr3 system is accompanied by a skeleton rearrangement and gives 6-dibromoalumo-7-methoxymethyl-2-menthene.Further hydroalumination affords a mixture of 2,6- and 2,5-bis(dibromoalumo)-7-(methoxymethyl)m

ALYLATION OF ALLYLIC CYCLOHEXENYL ESTERS WITH TRIALKYLALUMINIUM REAGENTS. A REGIO AND STEREOCHEMICAL STUDY

Regio and stereochemistry of the title reaction appear to be strongly influenced by the nature of both organometallic and allylic reagents.The results are discussed in view of the intervention of ion-pair intermediates.

REACTIONS OF p-TOLUENESULFONIC ACID TERPENE DERIVATIVES WITH LITHIUM IN ETHYLAMINE

Reactions of terpene p-toluenesulfonamides and p-toluenesulfonates with lithium in ethylamine were stated to afford, exclusively or mainly, respective amines and alcohols as the result of N-S or O-S bond cleavage.Presence of hydroxyl groups is not a hindrance. 2α-Hydroxy-3α-tosyloxypinane undergoes, partially, a rearrangement.The mechanism of that reaction is discussed.

REGIO AND STEREOSPECIFIC SYNTHESIS OF CIS AND TRANS 3-METHYL-6-METHYLETHYL CYCLOHEXENES AND 3-METHYL-4-METHYLETHYLCYCLOHEXENES. REACTIONS OF ALLYLIC ACETATES AND CARBAMATES WITH Li2Cu3Me5 AND LiCuMe2

The isomeric alkenes 1-4 have been obtained by syn, γ substitution of the appropriate allylic carbamates with Li2Cu3Me5.The behaviour of carbamates is deeply affected by the nature of the copper reagent.

Reaction of (+)carvomenthol tosylate with KCN in aprotic solvents; (1S,2R,4S) 1-methyl-4-isopropylcyclohexane-2-carbonitrile

Reaction of (+)carvomenthol tosylate with KCN in pyridine solution was proved to produce a mixture of hydrocarbons; in DMF additionally a small quantity of alcohols was obtained.However, in DMSO sterically homogeneous (-)(1S,2R,4S) 1-methyl-4-isopropylcyclohexane-2-carbonitrile ((-)neocarvomenthyl carbonitrile) was the main product.The structure of the compound obtained was determined on the basis of spectral data, elemental analysis, and chemical transformations which indicated configurational relation of the title compound to the known (-)(1S,2R,4S) neocarvomenthyl amine.