671211-41-9

Upstream product

• 67-56-1 methanol 
• 6485-40-1 (R)-Carvone 
• 127400-19-5 5-(1-(bromomethyl)-1-methoxyethyl)-2-methylcyclohex-2-enone 
• 2244-16-8 (S)-p-mentha-6,8-dien-2-one 
• 179093-74-4 (5R)-5-((2S)-1-Bromo-2-methoxypropan-2-yl)-2-methylcyclohex-2-enone 

Downstream Products

• 791854-79-0 (1S,4R,5R)-3-allyl-5-methoxy-1,5-dimethylbicyclo[2.2.2]octa-2,7-diene 

Relevant academic research and scientific papers

Bleach/Acetic Acid-Promoted Chlorinative Ring Expansion of [2.2.1]- and [2.2.2]-Bicycles

(Matrix Presented) Treatment of vinyl-substituted [2.2.1]- and [2.2.2]-bicyclocarbinols with NaOCI and AcOH provides [3.2.1]- and [3.2.2]-β-chloro-bicycloketones, respectively. For [2.2.2]-bicycles, these chlorinative ring expansions are particularly efficient and selective.

Enantio- and Diastereodivergent Sequential Catalysis Featuring Two Transition-Metal-Catalyzed Asymmetric Reactions

This study demonstrates the feasibility and inherent benefits of combining two distinct asymmetric transition-metal-catalyzed reactions in one pot. The reported transformation features a Pd-catalyzed asymmetric allylic alkylation and a Rh-catalyzed enantioselective 1,4-conjugate addition, effectively converting simple allyl enol carbonate precursors into enantioenriched cyclic ketones with two remote stereocenters. Despite the anticipated challenges associated with controlling stereoselectivity in such a complex system, the products are obtained in enantiomeric excesses ranging up to >99 % ee, exceeding those obtained from either of the individual asymmetric reactions. In addition, since the stereoselectivity of both steps is under catalyst control, this one-pot reaction is enantio- and diastereodivergent, enabling facile access to all stereoisomers from the same set of starting materials.

Synthesis of chiral bicyclo [2.2.2] oct-5-en-2-ones via an intramolecular alkylation reaction

Generation of the thermodynamic dienolate of 9-bromocarvone derivatives 5,7 and 11 furnished the chiral bicyclo[2.2.2]octenones 6, 8 and 9 and 12 and 13 containing a bridgehead methyl group via an intramolecular alkylation reaction. In an analogous manner