1349798-02-2

Upstream product

• 90-46-0 9-hydroxyxanthene 
• 104-53-0 3-phenyl-propionaldehyde 
• 1308401-12-8 (R)-3-phenyl-2-(9H-xanthen-9-yl)propanal 
• 92-83-1 xanthene 

Relevant academic research and scientific papers

Organocatalytic enantioselective dehydrogenative α-alkylation of aldehydes with benzylic compounds

The highly enantioselective cross-dehydrogenative coupling of aldehydes with benzylic compounds has been developed as an efficient and rapid protocol for synthesis of enantioriched α-alkylated aldehydes.

Asymmetric visible-light photoredox cross-dehydrogenative coupling of aldehydes with xanthenes

We report a methodology for the catalytic asymmetric cross-coupling of two C(sp3)-H bonds employing visible light as an economical and environmentally benign source of energy. Photoredox catalysis is used for the oxidation of a diarylmethane to the corresponding cation, which is then trapped by an enamine intermediate generated in situ from an aldehyde reactant and a secondary amine organocatalyst. Notably, this mild method is an ideal synthetic approach from the green chemistry point of view. It does not require preinstallation of functional groups, thereby constituting an atom economical, efficient transformation, and it allows the formation of a C-C bond with simultaneous installation of one or two new stereocenters in a highly enantio- and diastereoselective manner. Mechanistic studies by experimental and computational methods aid to clarify the origin of the observed enantioselectivity.

Merging organocatalysis with transition metal catalysis: Highly stereoselective α-alkylation of aldehydes

The unprecedented cooperative systems involving a diarylprolinol silyl ether with various Lewis acids have been found to effect the highly enantioselective intermolecular α-alkylation of aldehydes. A wide variety of aldehydes and alcohols can be transformed into the desired highly functionalized aldehydes in high yields, excellent enantioselectivities, and good diastereoselectivities at room temperature under mild conditions.

Highly enantioselective intermolecular alkylation of aldehydes with alcohols by cooperative catalysis of diarylprolinol silyl ether with Bronsted acid

Two cooperative systems: I/2,3,4-trihydroxybenzoic acid and I/TfOH effect highly enantioselective intermolecular α-alkylation of aldehydes. These systems afford functionalized aldehydes in high yields, and with excellent ee and de values with broad substrate scope (see scheme; R1=alkyl, R2,R3=aryl, or R2=ferrocenyl, R 3=phenyl, or R2=indolyl, R3=phenyl).