608489-13-0

Upstream product

• 145092-77-9 (1R,4R)-bicyclo[2.2.1]heptane-2,5-dione 
• 100-59-4 phenylmagnesium chloride 
• 608489-09-4 (1R,4R)-spiro[5-trifluoromethanesulfonyloxybicyclo[2.2.1]hept-5-ene-2,2'-[1,3]dioxolane] 
• 608489-10-7 (1R,4R)-spiro[5-benzylbicyclo[2.2.1]hept-5-ene-2,2'-[1,3]dioxolane] 
• 608489-11-8 (1R,4R)-2-benzyl[2.2.1]hept-2-en-5-one 
• 608489-08-3 (1R,4R)-spiro[bicyclo[2.2.1]heptan-5-one-2,2'-[1.3]dioxolane] 
• 121-46-0 bicyclo[2.2.1]hepta-2,5-diene 
• 916670-75-2 (1R,4R)-2,5-di(trifluoromethanesulfonyloxy)bicyclo[2.2.1]hepta-2,5-diene 
• 6921-34-2 benzylmagnesium chloride 
• 1589-82-8 phenylmagnesium bromide 
• 608489-12-9 (1R,4R)-2-benzyl-5-trifluoromethanesulfonyloxybicyclo[2.2.1]hepta-2,5-diene 

Relevant academic research and scientific papers

Chiral Supramolecular U-Shaped Catalysts Induce the Multiselective Diels-Alder Reaction of Propargyl Aldehyde

The Diels-Alder reaction, which is a traditional [4 + 2] cycloaddition with two carbon-carbon bond formations, is one of the most powerful tools to synthesize versatile and unique six-membered rings. We show that chiral supramolecular U-shaped boron Lewis acid catalysts promote the unprecedented multiselective Diels-Alder reaction of propargyl aldehyde with cyclic dienes. Independent from the substrate control, enantio-, endo/exo-, π-facial-, regio-, site-, and substrate-selectivities could be controlled by the present U-shaped catalysts. The obtained reaction products could access the concise synthesis of chiral diene ligands and a key intermediate of (+)-sarkomycin. The results presented here might partially contribute to the development of artificial enzyme-like supramolecular catalysts for multiselective reactions, which will be able to target organic compounds that have thus far eluded synthesis.

Expanding the C2-symmetric bicyclo[2.2.1]hepta-2,5-diene ligand family: Concise synthesis and catalytic activity in rhodium-catalyzed asymmetric addition

New C2-symmetric bicyclo[2.2.1]hepta-2,5-dienes bearing methyl and phenyl substituents at the 2 and 5 positions were prepared enantiomerically pure through a two-step sequence starting from the readily available bicyclo[2.2.1]hepta-2,5-dione. Due to the instability or volatility of these dienes, their isolation was achieved through the formation of the corresponding stable [RhCl(diene)]2 complexes. These chiral rhodium complexes displayed high activity and enantioselectivity (up to 99% ee) in the rhodium-catalyzed 1,4-addition and 1,2-addition of phenylboronic acid to cyclic enones and N-sulfonylimines, respectively.

A chiral chelating diene as a new type of chiral ligand for transition metal catalysts: Its preparation and use for the rhodium-catalyzed asymmetric 1,4-addition

As a new type of chiral ligand, a C2-symmetric norbornadiene derivative (1R,4R)-2,5-dibenzylbicyclo[2.2.1]hepta-2,5-diene (1) was prepared and used for the rhodium-catalyzed asymmetric addition of organoboron and -tin reagents to α,β-unsaturate