Linked Life Data

18551491

Source:http://linkedlifedata.com/resource/pubmed/id/18551491

Statements in which the resource exists as a subject.
PredicateObject
rdf:type
lifeskim:mentions
pubmed:issue
22
pubmed:dateCreated
2008-7-29
pubmed:abstractText
Novel trans-4-hydroxy-L-proline-derived N,N'-dioxides have been developed and used as efficient organocatalysts for the one-pot three-component Strecker reaction with an aldehyde, (1,1-diphenyl)methylamine, and TMSCN. Both aromatic and aliphatic aldehydes were found to be suitable substrates. The corresponding alpha-amino nitriles were obtained in high yields with up to 95 % ee (ee=enantiomeric excess) under mild conditions. Optically pure products could be obtained after a single recrystallization. The catalyst can be easily prepared from trans-4-hydroxy-L-proline and a diamine in three steps. Based on the experimental results and the observed absolute configurations of the products, a possible transition state has been proposed to explain the origin of the asymmetric induction.
pubmed:language
eng
pubmed:journal
pubmed:citationSubset
IM
pubmed:chemical
pubmed:status
MEDLINE
pubmed:issn
0947-6539
pubmed:author
pubmed:issnType
Print
pubmed:volume
14
pubmed:owner
NLM
pubmed:authorsComplete
Y
pubmed:pagination
6789-95
pubmed:dateRevised
2009-8-4
pubmed:meshHeading
pubmed:year
2008
pubmed:articleTitle
Asymmetric three-component Strecker reactions catalyzed by trans-4-hydroxy-L-proline-derived N,N'-dioxides.
pubmed:affiliation
Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu, China.
pubmed:publicationType
Journal Article, Research Support, Non-U.S. Gov't