Linked Life Data

18076175

Source:http://linkedlifedata.com/resource/pubmed/id/18076175

Statements in which the resource exists as a subject.
PredicateObject
rdf:type
lifeskim:mentions
pubmed:issue
1
pubmed:dateCreated
2008-1-2
pubmed:abstractText
An organocatalytic, enantioselective oxy-Michael addition to achiral gamma- and delta-hydroxy-alpha,beta-enones was developed. The key transformation is an unprecedented, asymmetric conjugate addition triggered by complexation between an in situ generated boronic acid hemiester and a chiral amine catalyst. Functionally, the intermediate amine-boronate complex acts as a chiral hydroxide surrogate or synthon. The resultant chiral beta-hydroxy-ketones are obtained in good to excellent yields and high ee following mild oxidative removal of the cyclic boronate. Natural products (R,12Z,15Z)-2-hydroxy-4-oxohenicosa-12,15-dienyl acetate and (+)-(S)-streptenol A were synthesized to demonstrate the utility of this reaction.
pubmed:grant
pubmed:commentsCorrections
pubmed:language
eng
pubmed:journal
pubmed:citationSubset
IM
pubmed:chemical
pubmed:status
MEDLINE
pubmed:month
Jan
pubmed:issn
1520-5126
pubmed:author
pubmed:issnType
Electronic
pubmed:day
9
pubmed:volume
130
pubmed:owner
NLM
pubmed:authorsComplete
Y
pubmed:pagination
46-8
pubmed:dateRevised
2011-5-11
pubmed:meshHeading
pubmed:year
2008
pubmed:articleTitle
Enantioselective, organocatalytic oxy-michael addition to gamma/delta-hydroxy-alpha,beta-enones: boronate-amine complexes as chiral hydroxide synthons.
pubmed:affiliation
Department of Biochemistry, University of Texas Southwestern Medical Center, Dallas, Texas 75390.
pubmed:publicationType
Journal Article, Research Support, Non-U.S. Gov't, Research Support, N.I.H., Extramural