105367-96-2

Upstream product

• 542-92-7 cyclopenta-1,3-diene 
• 140-88-5 ethyl acrylate 
• 1263187-14-9 3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-acrylic acid ethyl ester 

Downstream Products

• 95-12-5 (-)-(1S,2S,4S)-bicyclo[2.2.1]hept-5-en-2-yl methanol 
• 67671-06-1 (2R)-endo-5-norbornene-2-methanol 

Relevant academic research and scientific papers

Liquid coordination complexes of Lewis acidic metal chlorides: Lewis acidity and insights into speciation

Coordination complexes of Lewis acidic metal chlorides AlCl3, GaCl3, InCl3, SbCl3, SnCl4, SnCl2, ZnCl2 and TiCl4 with trioctylphosphine (P888) and trioctylphosphine oxide (P888O) were synthesised. All compounds formed liquid coordination complexes (LCCs) at ambient temperature, although decomposition via a redox mechanism was detected in some cases. The Lewis acidity of the metal chlorides (measured in 1,2-dichloroethane solutions) and the LCCs (measured neat) was quantified by using the Gutmann acceptor number (AN) approach. In general, LCCs were equally or more Lewis acidic than the corresponding metal chlorides. The AN values were compared with the catalytic activity of selected LCCs in a model Diels-Alder reaction. Insight into speciation of LCCs was gained using multinuclear NMR spectroscopy, revealing that most LCCs comprised charge-neutral complexes rather than ionic ones. The relationship between the speciation, Lewis acidity (AN scale) and catalytic activity is discussed in detail. This approach reveals several new, promising catalytic systems, such as P888O-InCl3, with Lewis acidity enhanced compared to chloroindate ionic liquids, and P888O-TiCl4, with hydrolytic stability enhanced with respect to neat TiCl4.

Design and Development of Highly Potent HIV-1 Protease Inhibitors with a Crown-Like Oxotricyclic Core as the P2-Ligand To Combat Multidrug-Resistant HIV Variants

Design, synthesis, and evaluation of a new class of exceptionally potent HIV-1 protease inhibitors are reported. Inhibitor 5 displayed superior antiviral activity and drug-resistance profiles. In fact, this inhibitor showed several orders of magnitude improved antiviral activity over the FDA approved drug darunavir. This inhibitor incorporates an unprecedented 6-5-5 ring-fused crown-like tetrahydropyranofuran as the P2 ligand and an aminobenzothiazole as the P2′ ligand with the (R)-hydroxyethylsulfonamide isostere. The crown-like P2 ligand for this inhibitor has been synthesized efficiently in an optically active form using a chiral Diels-Alder catalyst providing a key intermediate in high enantiomeric purity. Two high resolution X-ray structures of inhibitor-bound HIV-1 protease revealed extensive interactions with the backbone atoms of HIV-1 protease and provided molecular insight into the binding properties of these new inhibitors.

LiAlH4-induced reductive dephosphonylation of αα-dialkyl triethyl β-phosphonyl esters: Mechanistic study and synthetic application

Treatment of αα-dialkyl triethyl β-phosphonyl esters with LiAlHin CHlTHF caused the one-pot dephosphonylation and reduction to yield the corresponding primary alcohols bearing a controllable β secondary carbon center. Mechanistic study has revealed that the LiAlHinduced dephosphonylation should occur first with the assistance of the carboxylate group, and the hydrogen source of the resultant new C-H bond is LiAlH. Georg Thieme Verlag Stuttgart . New York.

Oxazaborolidine-derived Lewis acid assisted Lewis acid as a moisture-tolerant catalyst for enantioselective Diels-Alder reactions

Reactive, selective, and tough, the chiral Lewis acid generated from 1 and SnCl4 catalyzes the enantioselective Diels-Alder reactions of various classes of substrates (see scheme). The reactive species preserves its asymmetric induction ability even in the presence of a large excess of SnCl 4. Importantly, this catalyst system is tolerant to a small amount of moisture, oxygen, and Lewis bases.

Studies on the use of surfactants in aqueous Diels-Alder reactions

The effects of added surfactants on the aqueous Diels-Alder reaction between cyclopentadiene and a range of acrylate esters have been studied. The surfactants were used at their critical micellar concentrations, and the pH of the aqueous solutions was varied to determine the optimum conditions for the formation of the endo cycloadduct.

ASYMMETRIC DIELS-ALDER REACTIONS OF CHIRAL ALKOXY IMINIUM SALTS

The optically active vinyl trimethylsilyloxy iminium salts, prepared from 8 and 14ab, were reacted with cyclopentadiene to give the optically active amides 15 and 16ab in high yield and with good diastereoselectivity.