189210-87-5

Upstream product

• 124-63-0 methanesulfonyl chloride 
• 131063-54-2 (1S,2S,4S,5S)-(+)-1,4-dihydroxy-2,5-dimethylcyclohexane 
• 4074-22-0 1,4-dimethyl-cyclohexa-1,4-diene 
• 106-42-3 para-xylene 

Downstream Products

• 874292-41-8 Methanesulfonic acid (1S,2S,4R,5S)-4-azido-2,5-dimethyl-cyclohexyl ester 
• 874292-42-9 2,5-dimethyl-7-azabicyclo[2.2.1]heptane 

Relevant academic research and scientific papers

Syntheses of novel chiral 2,5-dialkyl-7-azabicyclo[2.2.1]heptanes and 2,5-dialkyl-7-thiobicyclo[2.2.1]heptanes

New C2-symmetric chiral amines with a rigid bicyclic framework have been synthesized via hydrogenation of monoazides catalyzed by 5% Pd/C in methanol. Enantiomerically pure 2,5-dialkyl-7-thiobicyclo[2.2.1]heptanes were made from readily available materials.

Chiral Bicyclo[2.2.2]octane-Fused CpRh Complexes: Synthesis and Potential Use in Asymmetric C?H Activation

A new class of chiral cyclopentadienyl rhodium(I) complexes (CpRhI) bearing C2-symmetric chiral bridged-ring-fused Cp ligands was prepared. The complexes were successfully applied to the asymmetric C?H activation reaction of N-methoxybenzamides with quinones, affording a series of chiral hydrophenanthridinones in up to 82 % yield with up to 99 % ee. Interestingly, structure analysis reveals that the side wall of the optimal chiral CpRhI catalyst is vertically more extended, horizontally less extended, and closer to the metal center in comparison with the classic binaphthyl and spirobiindanyl CpRhI complexes, and may thus account for its superior catalytic performance.

C2-Symmetric nitroxides and their potential as enantioselective oxidants

The synthesis and evaluation of four C2-symmetric nitroxides are presented. The nitroxides were evaluated for their ability to mediate the oxidation of several alcohols and found to have good catalytic activity. One enantioenriched nitroxide was found to kinetically resolve selected secondary alcohols with very modest selectivities.

Highly enantioselective hydrogenation of simple ketones catalyzed by a Rh-PennPhos complex

Even alkyl methyl ketones undergo asymmetric hydrogenation with high enantioselectivity when a rhodium complex of the conformationally rigid chiral ligand 1 (Me-PennPhos; R = CH3) is used as the catalyst. Basic additives such as 2,6-lutidine contribute to the achievement of high enantiomeric excesses.