96206-30-3

Upstream product

• 25866-56-2 (+/-)-5,5-dimethylcyclohex-2-en-1-ol 
• 822-67-3 Cyclohex-2-enol 
• 4694-17-1 5,5-dimethlycyclohex-2-en-1-one 

Downstream Products

• 113647-34-0 (S)-(5,5-Dimethyl-cyclohex-2-enyl)-[(1R,4R)-1,7,7-trimethyl-bicyclo[2.2.1]hept-(2E)-ylideneamino]-acetic acid tert-butyl ester 
• 113647-34-0 (R)-(5,5-Dimethyl-cyclohex-2-enyl)-[(1R,4R)-1,7,7-trimethyl-bicyclo[2.2.1]hept-(2E)-ylideneamino]-acetic acid tert-butyl ester 
• 597-43-3 2,2-dimethylsuccinic acid 
• 4839-46-7 3,3-Dimethylglutaric acid 
• 1028207-21-7 N-(2-bromo-benzyl)-5,5-dimethylcyclohex-2-enyl-amine 
• 1241732-58-0 (S)-(2-(5,5-dimethylcyclohex-2-en-1-yl)ethyl)benzene 

Relevant academic research and scientific papers

Guanidine–Copper Complex Catalyzed Allylic Borylation for the Enantioconvergent Synthesis of Tertiary Cyclic Allylboronates

An enantioconvergent synthesis of chiral cyclic allylboronates from racemic allylic bromides was achieved by using a guanidine–copper catalyst. The allylboronates were obtained with high γ/α regioselectivities (up to 99:1) and enantioselectivities (up to 99 % ee), and could be further transformed into diverse functionalized allylic compounds without erosion of optical purity. Experimental and DFT mechanistic studies support an SN2′ borylation process catalyzed by a monodentate guanidine–copper(I) complex that proceeds through a special direct enantioconvergent transformation mechanism.

Copper-catalyzed asymmetric allylic alkylation of racemic cyclic substrates: Application of dynamic kinetic asymmetric transformation (DYKAT)

The copper-catalyzed asymmetric allylic alkylation (AAA) is of great interest in organic synthesis. This reaction was extensively studied using a broad range of substrates, ligands and organometallic reagents. However, the use of racemic substrates was still limited. Although some processes of kinetic resolution are reported in the literature, no examples of quantitative deracemization are described as is the case for the Pd-catalyzed allylic alkylation. We present here a full account of our investigations through the development of the first example of such a process in copper-catalyzed AAA. High enantioselectivities (up to 99% ee), scope of the reaction and mechanistic considerations are reported herein.

A study of Heck cyclization reactions to form phenanthridine ring systems

A survey of conditions for the palladium catalyzed intramolecular Heck cyclization of protected amines has shown that the Herrmann-Beller palladacycle can be exploited under 'cationic' conditions to provide a robust and rapid route (2 h) to the synthesis