260967-07-5

Upstream product

• 183444-01-1 (1-benzenesulfonyl-3-phenyl-propyl)-carbamic acid benzyl ester 
• 104-53-0 3-phenyl-propionaldehyde 
• 621-84-1 O-benzyl carbamate 

Relevant academic research and scientific papers

Chiral Alkyl Amine Synthesis via Catalytic Enantioselective Hydroalkylation of Enecarbamates

Chiral alkyl amines are omnipresent as bioactive molecules and synthetic intermediates. The catalytic and enantioselective synthesis of alkyl amines from readily accessible precursors is challenging. Here we develop a nickel-catalyzed hydroalkylation method to assemble a wide range of chiral alkyl amines from enecarbamates (N-Cbz-protected enamines) and alkyl halides with high regio- and enantioselectivity. The method works for both nonactivated and activated alkyl halides and is able to produce enantiomerically enriched amines with two minimally differentiated α-alkyl substituents. The mild conditions lead to high functional group tolerance, which is demonstrated in the postproduct functionalization of many natural products and drug molecules, as well as the synthesis of chiral building blocks and key intermediates to bioactive compounds.

A stereoselective synthesis of primary (Z)-enecarbamates from α- amidoalkylphenyl sulfones

A base assisted elimination of phenylsulfinic acid from α- amidoalkylphenyl sulfones leads to the synthesis of the corresponding enecarbamates. The Z stereoisomer of the enecarbamate is preferentially formed.