Journal of Organic Chemistry 2013-02-15

Copper(I) halide promoted diastereoselective synthesis of chiral propargylamines and chiral allenes using 2-dialkylaminomethylpyrrolidine, aldehydes, and 1-alkynes.

Ramani Gurubrahamam, Mariappan Periasamy

Index: J. Org. Chem. 78(4) , 1463-70, (2013)

Full Text: HTML

Abstract

Copper bromide promoted reactions of aldehydes, 1-alkynes, and chiral 2-dialkylaminomethylpyrrolidine at 25 °C give the corresponding chiral propargylamine derivatives in up to 96% yield and 99:1 dr that are readily converted to the corresponding disubstitued chiral allenes in up to 81% yield and 99% ee upon reaction with CuI in dioxane at 100 °C.

Related Compounds

  • pargyline hydrochl...
  • Prop-2-yn-1-aminiu...

Related Articles:

Chemical genetics reveals a complex functional ground state of neural stem cells.

2007-05-01

[Nat. Chem. Biol. 3(5) , 268-273, (2007)]

Genetic mapping of targets mediating differential chemical phenotypes in Plasmodium falciparum.

2009-10-01

[Nat. Chem. Biol. 5 , 765-71, (2009)]

Azure B and a synthetic structural analogue of methylene blue, ethylthioninium chloride, present with antidepressant-like properties.

2014-11-11

[Life Sci. 117(2) , 56-66, (2015)]

Origins of stereoselectivities in chiral phosphoric acid catalyzed allylborations and propargylations of aldehydes.

2013-02-01

[J. Org. Chem. 78(3) , 1208-15, (2013)]

Divergent reaction pathways of homologous and isosteric propargyl amides in sequential Ru/Pd-catalyzed annulations for the synthesis of heterocycles.

2013-04-19

[J. Org. Chem. 78(8) , 3832-46, (2013)]

More Articles...