81600-63-7

Upstream product

• 35836-73-8 (1R)-(-)-nopol 
• 98-59-9 p-toluenesulfonyl chloride 

Downstream Products

• 144341-95-7 (-)-(1R,2R)-2,3-Epoxy-6,6-dimethylbicyclo<3.1.1>heptane-2-ethyl 4-toluenesulfonate 
• 140465-27-6 N-phenyl-6,6-dimethylbicyclo<3.1.1>hept-2-ene-2-ethanamine 
• 140465-24-3 N-benzyl-6,6-dimethylbicyclo<3.1.1>hept-2-ene-2-ethanamine 
• 608132-53-2 5,5-dimethyl-2-(2-(p-acetylphenoxy)ethyl)bicyclo[3.1.1]hept-2-ene 
• 35836-72-7 nopyl acetate 
• 140632-14-0 nopylamine 
• 144342-07-4 (+)-(4R)-5,5-Dimethyl-4-(2-oxoethyl)cyclopent-1-ene-1-ethyl 4-toluenesulfonate 

Relevant academic research and scientific papers

A study of transesterification of chiral (-)-pinanediol methylboronic ester with various structurally modified diols

The transesterification of chiral (-)-pinanediol methylboronic ester was studied with various structurally modified diols by 1H NMR to understand the factors influencing the unusual stability of this boronic ester as well as to find ways of recovering pinanediol from its methylboronic ester. In all the cases, reactions were allowed to proceed to equilibrium. The preliminary experiments indeed have shown some encouraging results (displacement of pinanediol up to 40-53%). Amongst cyclopentane-based cis-1,2-diols, endo-2-phenyl-exo,exo-2,3-norbornane-diol appeared to be the most effective diol in displacing pinanediol (38%). In the cases of pinane-based diols, the best result was obtained with 2-ethyl-6,6-dimethylbicyclo[3.1.1]heptane-cis-2,3-diol (53%). It was interesting to observe that the transesterification with 2-phenyl-6,6-dimethylbicyclo[3.1.1]heptane-cis-2,3-diol resulted in a 50% conversion after 4 days only, whereas the former diol took 24 days to reach equilibrium.

Optically active transition-metal complexes. I. Iron, cobalt and rhodium complexes of the optically active diolefin (+)-nopadiene and its derivatives. The crystal structure of C5Me5Rh(nopadiene)

The syntheses of metal complexes of the optically active diolefins nopadiene, acetylnopadiene, nopadiene acid and nopadiene aldehyde are described.All the ligands were coordinated to the Fe(CO)3 group and some also to CpRh, CpCo, Cp*Rh and Cps

Synthesis and phytotoxicity of new ionic liquids incorporating chiral cations and/or chiral anions

The aim of this work was to synthesize chiral ionic liquids as chiral solvents for organic synthesis and to evaluate the phyto(eco)toxicity of the new products and starting N-alkylimidazoles and their potential environmental influence on soil and plants.

First study of rhodium(I) complexes with chiral sulfur-containing terpenoids as catalytic systems for ketone hydrosilylation

Using a “chiral pool” approach, a number of chiral thiolate and sulfide ligands based on natural terpenes and terpenoids have been synthesized in a few simple steps. Two new Rh-thiolate complexes with the formula [Rh(CO)2(μ-SR)]2 were obtained. The influence of these complexes and catalytic systems formed by combining the synthesized ligands with [Rh(CO)2(μ-Cl)]2 and [Rh(cod)(μ-Cl)]2, on the reaction rate, chemoselectivity, stereoselectivity and formation of tetraphenyldisiloxane in Rh-catalyzed asymmetric hydrosilylation of acetophenone as a model reaction have been studied. Mechanistic aspects of formation of silyl enol ether as a side product in the presence of S-containing ligands are presented.

Reactivity of dipinanyl diselenides functionalized at the C-10-position with-CH2O(Se)Ph,-OH and-OCPh3 substituents

Terpenyl alcohols, (-)-nopol and (-)-myrtenol were efficiently applied in the synthesis of new diselenides. The pinane skeleton, as the core of the structure, was decorated at the C-10 position by hydroxyl and O-trityl groups, and also OPh and SePh substi

Fast and Tight Boronate Formation for Click Bioorthogonal Conjugation

A new click bioorthogonal reaction system was devised to enable the fast ligation (kON≈340 m-1 s-1) of conjugatable derivatives of a rigid cyclic diol (nopoldiol) and a carefully optimized boronic acid partner, 2-methyl-5-carboxymethylphenylboronic acid. Using NMR and fluorescence spectroscopy studies, the corresponding boronates were found to form reversibly within minutes at low micromolar concentration in water, providing submicromolar equilibrium constant (Keq≈105-106 m-1). Efficient protein conjugation under physiological conditions was demonstrated with model proteins thioredoxin and albumin, and characterized by mass spectrometry and gel electrophoresis.

Asymmetric synthesis using organoboranes. Relative effectiveness of the B-Halobis(terpenyl)boranes for the enantioselective halogenative cleavage of representative meso-epoxides

A comparative study of the relative effectiveness of various Ter 2BX, such as dEap2BX, lEap 2BX, 2-dIcr2BX, 4-dIcr 2BX, and lCleap2BX

Intramolecular photosensitization of the pinene-ocimene rearrangement

Bonding of nopol to the para position of acetophenone produces 5,5-dimethyl-2-(2-(p-acetylphenoxy)ethyl)bicyclo[3.1.1]hept-2-ene 1, which contains two chromophores: a para-alkoxyacetophenone and an α-pinene, connected by a single methylene group. UV irrad

Synthesis of cardamom peroxide analogues by radical cyclization of hydroperoxyalkenes

Three pinenic hydroperoxides were synthesized according to the Dussault method. Two of them could cyclize under radical conditions to give the exo-trig isomer as a single regioisomer. Only five- and six-member ring peroxides were obtained, whereas none of

B-iso-2-(2-diethylaminoethyl)apopinocampheyl-9-borabicyclo-[3.3.1]nonyl hydride - An improved chiral reducing agent for straight chain aliphatic ketones

A series of chirally modified borohydrides of the type lithium B-iso-2- (alkyl)apopinocampheyl-9-borabicyclo[3.3.1]nonyl hydride (2-4 and 8-9) were prepared to enable a strategic development of chiral reagents for the reduction of straight chain aliphatic ketones. Reagent 8 (alkyl = 2- diethylaminoethyl) reduces 2-octanone in 82% ee, significantly higher than that obtained with NB-Enantride (7) under identical conditions. An improved methodology for these reductions is also described.