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Direct carbon-carbon bond formation via reductive soft enolization: a kinetically controlled syn-aldol addition of α-halo thioesters and enolizable aldehydes.

dc.contributor.author Coltart, Dr Don
dc.contributor.author Garnsey, Michelle R
dc.contributor.author Sauer, Scott J
dc.coverage.spatial United States
dc.date.accessioned 2011-06-21T17:26:22Z
dc.date.accessioned 2016-06-21T22:32:50Z
dc.date.issued 2010-10-13
dc.identifier http://www.ncbi.nlm.nih.gov/pubmed/20849119
dc.identifier.uri http://hdl.handle.net/10161/12403
dc.description.abstract The direct addition of enolizable aldehydes and α-halo thioesters to produce β-hydroxy thioesters enabled by reductive soft enolization is reported. The transformation is operationally simple and efficient and has the unusual feature of giving high syn-selectivity, which is the opposite of that produced for (thio)esters under conventional conditions. Moreover, excellent diastereoselectivity results when a chiral nonracemic α-hydroxy aldehyde derivative is used.
dc.language eng
dc.language.iso en_US
dc.relation.ispartof J Am Chem Soc
dc.relation.isversionof 10.1021/ja1057407
dc.relation.replaces http://hdl.handle.net/10161/4045
dc.relation.replaces 10161/4045
dc.subject Aldehydes
dc.subject Carbon
dc.subject Esters
dc.subject Kinetics
dc.subject Oxidation-Reduction
dc.title Direct carbon-carbon bond formation via reductive soft enolization: a kinetically controlled syn-aldol addition of α-halo thioesters and enolizable aldehydes.
dc.title.alternative
dc.type Journal article
dc.description.version Version of Record
duke.date.pubdate 2010-10-13
duke.description.issue 40
duke.description.volume 132
dc.relation.journal Journal of the American Chemical Society
pubs.author-url http://www.ncbi.nlm.nih.gov/pubmed/20849119
pubs.begin-page 13997
pubs.end-page 13999
pubs.issue 40
pubs.organisational-group Duke
pubs.organisational-group Staff
pubs.publication-status Published
pubs.volume 132
dc.identifier.eissn 1520-5126


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