Chemical Communications 2012-11-04

Kinetic resolution of propargylamines via a highly enantioselective non-enzymatic N-acylation process.

Amandine Kolleth, Sarah Christoph, Stellios Arseniyadis, Janine Cossy

Index: Chem. Commun. (Camb.) 48(85) , 10511-3, (2012)

Full Text: HTML

Abstract

The non-enzymatic kinetic resolution of diversely substituted primary propargylic amines is reported featuring a highly selective acetyl transfer using (1S,2S)- in conjunction with Aliquat(TM) 336, affording the corresponding enantio-enriched N-acetylated propargylic amines with unprecedented levels of selectivity (s-factors of up to 193 at 50% conversion).


Related Compounds

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...