Scalable organocatalytic asymmetric Strecker reactions catalysed by a chiral cyanide generator

Hailong Yan, Joong Suk Oh, Ji-Woong Lee and Choong Eui Song ()
Additional contact information
Hailong Yan: Sungkyunkwan University
Joong Suk Oh: Sungkyunkwan University
Ji-Woong Lee: Sungkyunkwan University
Choong Eui Song: Sungkyunkwan University

Nature Communications, 2012, vol. 3, issue 1, 1-7

Abstract: Abstract The Strecker synthesis is one of the most facile methods to access racemic α-amino acids. However, feasible catalytic asymmetric Strecker reactions for the large-scale production of enantioenriched α-amino acids are rare. Here we report a scalable catalytic asymmetric Strecker reaction that uses an accessible chiral variant of oligoethylene glycol as the catalyst and KCN to generate a chiral cyanide anion. Various α-amido sulphone substrates (alkyl, aryl and heteroaryl) can be transformed into the optically enriched Strecker products, α-aminonitriles, with excellent yields and enantioselectivities. Moreover, the robust nature of the catalyst enables a ‘one-pot’ synthesis of enantiomerically pure α-amino acids starting from α-amido sulphones and simple catalyst recycling. These features can make this protocol easily adaptable to the practical synthesis of unnatural α-amino acids.

Date: 2012
References: Add references at CitEc
Citations:

Downloads: (external link)
https://www.nature.com/articles/ncomms2216 Abstract (text/html)

Related works:
This item may be available elsewhere in EconPapers: Search for items with the same title.

Export reference: BibTeX RIS (EndNote, ProCite, RefMan) HTML/Text

Persistent link: https://EconPapers.repec.org/RePEc:nat:natcom:v:3:y:2012:i:1:d:10.1038_ncomms2216

Ordering information: This journal article can be ordered from
https://www.nature.com/ncomms/

DOI: 10.1038/ncomms2216

Access Statistics for this article

Nature Communications is currently edited by Nathalie Le Bot, Enda Bergin and Fiona Gillespie

More articles in Nature Communications from Nature
Bibliographic data for series maintained by Sonal Shukla () and Springer Nature Abstracting and Indexing ().