22038-83-1

Usage

Physical state

Clear, colorless liquid

Odor

Strong amine odor

Chirality

Chiral amine compound

Common uses

Intermediate in the synthesis of pharmaceuticals and fine chemicals, precursor in the production of pesticides, reagent in organic synthesis

Versatility

Potential applications in a wide range of industries

Chiral nature

Valuable building block in the development of asymmetric synthesis methodologies.

Upstream product

• 138234-65-8 (1R,1'R)-2'-Hydroxy-1'-(phenylethyl)-1-(1-naphthyl)-propylamine 

Relevant academic research and scientific papers

1,2- vs 1,4-Addition of Nucleophilic Organometallics to Nonracemic 2-(1-Naphthyl)- and 2-Cinnamyl-1,3-oxazolidines

We herein report our results where the addition of organomagnesium reagents to 2-(1-naphthyl)- and 2-cinnamyl-1,3-oxazolidines occurred consistently in a 1,4-conjugate manner, while lithium, cerium and copper organometallic reagents added in a 1,2 fashion.The 1,4-conjugate addition pathway was primarely exploited by using (4R)-2-(1-naphthyl)-4-phenyl-1,3-oxazolidine (4) as a substrate to obtain, after NaBH4 reduction of the intermediate aldehyde, trans-disubstituted 1,2-dihydronaphthalenes with enantiomeric excess of 93-94percent.The amino alcohol products resulting from1,2-addition were oxidatively cleaved to afford enantiomeric enriched (R)-α-(1-naphthyl)alkylamines 6a and 6b in 99percent ee.